Name: 1664-40-0|N-Phenylethylenediamine|95%
Brand: Ambeed
SKU: A814681
Price: 18.0 USD
Availability: InStock
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1
[ 2002-24-6 ]
[ 142-04-1 ]
[ 1664-40-0 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1955,vol. 75,p. 1318,1319,1321
Chem.Abstr.,1956,p. 10106

2
[ 75-15-0 ]
[ 1664-40-0 ]
[ 16099-65-3 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3048 - 3061
[2]Chemische Berichte,1891,vol. 24,p. 2197
[3]Zeitschrift fur Anorganische und Allgemeine Chemie,2015,vol. 641,p. 1728 - 1736
[4]Journal of Organometallic Chemistry,2018,vol. 861,p. 112 - 124

3
[ 1664-40-0 ]
[ 57-13-6 ]
[ 1848-69-7 ]

Reference： [1]Patent: US2517750,1943,

4
[ 124-38-9 ]
[ 1664-40-0 ]
[ 1848-69-7 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 7339 - 7342

5
[ 2065-37-4 ]
[ 1664-40-0 ]
[ 92887-71-3 ]

Reference： [1]Archiv der Pharmazie,1984,vol. 317,p. 743 - 749

6
[ 1664-40-0 ]
[ 501-53-1 ]
[ 101288-83-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1099 - 1104
[2]Organic Letters,2005,vol. 7,p. 2465 - 2468
[3]Chemical and Pharmaceutical Bulletin,1987,vol. 35,p. 2825 - 2839

7
[ 89711-08-0 ]
[ 1664-40-0 ]
[ 174497-02-0 ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 1066 - 1072

8
[ 24424-99-5 ]
[ 1664-40-0 ]
N-t-Butoxycarbonyl-N'-phenylethylenediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With 1,3-disulfonic acid imidazolium hydrogen sulfate; In neat (no solvent); at 20℃; for 0.0166667h;Green chemistry;	General procedure: Amine (1 mmol) was added to the mixture of (Boc)2O (1 mmol) and DSIMHS (6.5 mg, ~ 0.02 mmol) with constant stirring at room temperature under solvent-free conditions. After completion of the reaction (monitored by TLC), ethyl acetate (3 × 5 mL) was added to the reaction mixture and the catalyst was decanted and washed with ethyl acetate (2 × 5 mL) and dried. The product was purified by column chromatography, using ethyl acetate-petroleum ether (2:8) eluent.
87%	With sulfonic acid-functionalized nanoporous titania catalyst; In neat (no solvent); at 20℃; for 0.15h;	General procedure: An amine (1 mmol) was added to a magnetically stirred mixture of TiO2-Pr-SO3H (10 mg) and di-tert-butyl dicarbonate (240 mg, 1.1 mmol) at room temperature. The mixture was stirred until completion of the reaction (TLC), then diluted with EtOAc (10 mL) and filtered. The residue contains only the catalyst and kept for recovery. The filtrate was washed with water (3 x 20 mL) and brine (2 x 20 mL) and dried over anhydrous MgSO4, then solvent was distillated off under vacuum to yield the highly pure N-Boc derivative.
	In chloroform;	(i) Synthesis of t-butyl N-(2-anilinoethyl)carbamate(274) To a solution of <strong>[1664-40-0]N-phenylethylenediamine</strong> [10.3 g(75.4 mmol.)] in chloroform(120 ml) was added di-tert-butyl dicarbonate [16.5 g(75.4 mmol.)], and the mixture was stirred for two hours at room temperature. The solvent was distilled off to leave a powdery product, which was washed with hexane and dried to obtain the compound(274) [17.3 g(97.0%)] as pale yellow powder. IR(KBr)cm-1: 3390(br), 1680(br), 1610. NMR(90 MHz,CDCl3) delta: 1.50(9H,s), 3.25(2H,m), 3.71(2H,m), 4.90(1H,m), 6.47 to 7.33(5H,m).

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 7665 - 7669
[2]Journal of Molecular Liquids,2013,vol. 177,p. 386 - 393
[3]Journal of the Iranian Chemical Society,2013,vol. 10,p. 181 - 188
[4]RSC Advances,2015,vol. 5,p. 19790 - 19798
[5]Journal of Organometallic Chemistry,2013,vol. 745-746,p. 42 - 49
[6]Patent: US4962113,1990,A

9
[ 2576-47-8 ]
[ 62-53-3 ]
[ 1664-40-0 ]

Yield	Reaction Conditions	Operation in experiment
87%		A solution of 2-bromoethylamine hydrobromide (1.1 g, 5.4 mmol) and aniline (3.0 g, 32 mmol) in toluene (8 ml) was stirred for 1 day at 120 C under an argon atmosphere and the precipitated product was collected by filtration. The salt was then treated with a 20% aqueous NaOH solution and extracted with dichloromethane. The organic phase was dried over anhydrous Na2SO4. After the Na2SO4 was filtered out and the solvent was distilled the crude product was further purified by column chromatography on silica gel (eluant: methanol) to afford N-phenylethylenediamine as a red-brown liquid. Yield: 87% (0.64 g); 1H NMR (400 MHz, CDCl3) delta 1.51 (br s, 3H), 2.93 (t, 2H), 3.17 (t, 2H), 6.63 (d, 2H), 6.70 (t, 1H), 7.17 (t, 2H). 2-(Chloromethyl)pyridine hydrochloride (1.8 g, 11 mmol) was treated with a 20% aqueous NaOH solution and extracted with dichloromethane and the organic phase was dried over anhydrous Na2SO4. After Na2SO4 was filtered out and the solvent was evaporated off, a solution of 2-(chloromethyl)pyridine in benzene (3 ml) was added to a solution of N-phenylethylenediamine (0.69 g, 5.1 mmol), which was prepared as described above, and triethylamine (5.1 g, 51 mmol) in benzene (4 ml) and stirred for 17 h at 80 C under an argon atmosphere. After being cooled to room temperature and the addition of diethyl ether, the inorganic by-products were removed by washing with a saturated NaHCO3 solution and with brine. The organic phase was dried over anhydrous Na2SO4. After the Na2SO4 was filtered out and the solvent was removed the crude product was purified by column chromatography on silica gel (eluant: ethyl acetate) to afford 2a as a red-brown viscous liquid. Yield: 69% (1.1 g);
66%		General procedure: A mixture of aniline (or PhNHEt) (0.05 mol)), 2-bromoethyl- (or 3-bromopropyl)amine hydrobromide and water (6 mL) was heated to 95 C (ina bath), Then, NaHCO3 was added in small portions with stirring. After ~15 min (at 95 C), the reaction mixture was refluxed with stirring using a heating mantle until reaction reached completion. The amount of hydrobromide and NaHCO3 and the timeof heating are given in Table 1. Still warm reaction mixture was diluted with 50% aqueous KOH (11 mL) and water (16 mL). The organic layer was separated, the aqueous layer was saturated with NaCl and extracted with chloroform (4×20 mL), each timeadding NaCl into the aqueous phase. The combined organic layers were dried with MgSO4 and fractionally distilled in vacuo.
62%	With potassium hydroxide; In water; toluene; for 18h;Reflux;	2-Bromoethylamine hydrobromide (0.1 mmol)And aniline (1)(0.25 mmol) was added to 40 mlIn toluene was heated at reflux for 18 hours,cool down.Water (60 ml) was added20 ml of a 50% aqueous KOH solution,The layers were allowed to stand.The aqueous phase was washed with saturated NaCl and extracted three times with dichloromethane.The organic phases were combined and washed with saturated NaCl,Anhydrous Na2SO4 dry,Filtered and evaporated to dryness.Column layerThe pure compound (2)Yield 62%.

In toluene; for 5h;Reflux;

General procedure: To a stirred solution of 5a-l (21mmol) in anhydrous toluene (40mL) was added compounds 6, 7 (7mmol) at room temperature. The mixture was refluxed for 5h, cooled to room temperature and filtered. The filtered solid was treated with NaOH solution (1M, 50mL) and extracted by DCM (50mL×3). The combined extraction was dried over anhydrous MgSO4 and filtered. The filtration was concentrated to yield the crude compounds 8a-l, 9a-d which were not further purified and used directly for the next step.

Reference： [1]Tetrahedron,2011,vol. 67,p. 6927 - 6933
[2]Synthesis,2004,p. 851 - 856
[3]Russian Chemical Bulletin,2016,vol. 65,p. 2211 - 2215
Izv. Akad. Nauk, Ser. Khim.,2016,p. 2211 - 2215,5
[4]Patent: CN103948587,2016,B .Location in patent: Paragraph 0031; 0054; 0055
[5]Canadian Journal of Chemistry,2004,vol. 82,p. 1649 - 1661
[6]Journal of Medicinal Chemistry,1997,vol. 40,p. 3369 - 3380
[7]European Journal of Medicinal Chemistry,2017,vol. 137,p. 117 - 125

10
[ 87233-54-3 ]
[ 1664-40-0 ]
[ 110-17-8 ]
2-amino-1-(2-ethoxyethyl)-N-(2-phenylaminoethyl)-1H-benzimidazole hydrogen fumarate [ No CAS ]

Reference： [1]Heterocycles,1999,vol. 51,p. 2561 - 2573

11
[ 1664-40-0 ]
[ 207557-35-5 ]
(S)-1-[2-(2-Phenylamino-ethylamino)-acetyl]-pyrrolidine-2-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 2774 - 2789

12
[ 1664-40-0 ]
[ 380151-85-9 ]
1-phenyl-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]imidazolidine [ No CAS ]

Reference： [1]New Journal of Chemistry,2003,vol. 27,p. 1419 - 1424

13
[ 1664-40-0 ]
[ 530-62-1 ]
[ 1848-69-7 ]

Reference： [1]Canadian Journal of Chemistry,2004,vol. 82,p. 1649 - 1661

14
[ 911389-82-7 ]
[ 1664-40-0 ]
[ 1000850-90-7 ]

Yield	Reaction Conditions	Operation in experiment
49%	In tetrahydrofuran; at 0℃;	Step 1. 1-(4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-3-(2-(phenylamino)ethyl)urea (75) <strong>[1664-40-0]N-phenylethylenediamine</strong> (0.062 ml, 0.477 mmol) was added to a solution of compound 68 (0.207 g, 0.477 mmol) in THF (4.77 mL) at 0 C. and the mixture was stirred overnight. The reaction mixture was diluted with EtOAc then water and aqueous sodium bicarbonate was added and the mixture was stirred. The resultant suspension was filtered and the solid thus collected was washed with additional water and EtOAc then dried under vacuum to afford compound 75 (0.111 g, 49% yield) as white solid. MS (m/z): 477.2 (M+H).

Reference： [1]Patent: US2008/4273,2008,A1 .Location in patent: Page/Page column 78

15
[ 4422-95-1 ]
[ 1664-40-0 ]
N-1,3,5-tris[2-(phenylamino)ethyl]benzene-1,3,5-tricarboxylamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7458 - 7467
[2]Journal of Fluorescence,2019,vol. 29,p. 375 - 385

16
(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid [ No CAS ]
N-benzyl-1-(diphenylacetyl)-4-(methoxyimino)-2-pyrrolidinecarboxamide [ No CAS ]
[ 4385-76-6 ]
[ 1664-40-0 ]
(2S,4EZ)-N-(2-anilinoethyl)-4-(methoxyimino)-1-[4-(4-pyridinyl)benzoyl]-2-pyrrolidinecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		(2S,4EZ)-N-(2-anilinoethyl)-4-(methoxyimino)-1-[4-(4-pyridinyl)benzoyl]-2-pyrrolidinecarboxamide Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid, <strong>[4385-76-6]4-(4-pyridinyl)benzoic acid</strong>, and N1-phenyl-1,2-ethanediamine, the title compound was obtained in 85percent purity by HPLC. MS(ESI+): m/z=458.

Reference： [1]Patent: US2003/171309,2003,A1

17
(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid [ No CAS ]
N-benzyl-1-(diphenylacetyl)-4-(methoxyimino)-2-pyrrolidinecarboxamide [ No CAS ]
[ 1664-40-0 ]
[ 4385-75-5 ]
(2S,4EZ)-N-(2-anilinoethyl)-4-(methoxyimino)-1-[4-(3-pyridinyl)benzoyl]-2-pyrrolidinecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		(2S,4EZ)-N-(2-anilinoethyl)-4-(methoxyimino)-1-[4-(3-pyridinyl)benzoyl]-2-pyrrolidinecarboxamide Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid, 4-(3-pyridinyl)benzoic acid, and N1-phenyl-1,2-ethanediamine, the title compound was obtained in 85%purity by HPLC. MS(ESI+): m/Z=458.

Reference： [1]Patent: US2003/171309,2003,A1

18
[ 4385-62-0 ]
(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid [ No CAS ]
[ 1664-40-0 ]
(2S,4EZ)-N-(2-anilinoethyl)-4-(methoxyimino)-1-[4-(2-pyridinyl)benzoyl]-2-pyrrolidinecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		(2S,4EZ)-N-(2-anilinoethyl)-4-(methoxyimino)-1-[4-(2-pyridinyl)benzoyl]-2-pyrrolidinecarboxamide Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid, 4-(2-pyridinyl)benzoic acid, and N1-phenyl-1,2-ethanediamine, the title compound was obtained in 67% purity by HPLC. MS(ESI+): m/z=458.

Reference： [1]Patent: US2003/212012,2003,A1

19
[ 75-44-5 ]
[ 3612-20-2 ]
1-benzyl-4-(2-phenylamino-1-ethylamino)-piperidine [ No CAS ]
[ 1664-40-0 ]
[ 61220-54-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide;platinum; In methanol; water; toluene;	9.8 g of <strong>[1664-40-0]N-phenylethylenediamine</strong> and 13.9 g of 1-benzyl-4-piperidone are dissolved in 200 ml of methanol and, with the addition of 0.7 g of a 5% platinum on charcoal catalyst, hydrogenated at room temperature and under normal pressure. The calculated amount of hydrogen is taken up after approx. 3 hours. The reaction mixture is filtered to remove the catalyst and concentrated in a water jet vacuum. The residue crystalises from methanol/water to yield 21.4 g of 1-benzyl-4-(2-phenylamino-ethylamino)-piperidino with a melting point of 78-81 C. With stirring, 15 g of phosgene are introduced at 5 to 10 C in the course of 1 hour into a suspension of 10 g of 1-benzyl-4-(2-phenylamino-1-ethylamino)-piperidine in 100 ml of toluene and 48.5 ml of 3N potassium hydroxide solution. After stirring for 2 hours at 5 to 10 C, the reaction mixture is made alkaline with 43 ml of 6N potassium hydroxide solution and brought to room temperature. After it has been stirred for a further 15 hours at room temperature, the reaction mixture is filtered with suction and the residue is recrystallized from isopropanol-methanol to yield 7.2 g of 1-(1-benzyl-4-piperidinyl)-3-phenyl-2-imidazolidinone.

Reference： [1]Patent: US4144344,1979,A

20
[ 28920-43-6 ]
[ 1664-40-0 ]
[ 947528-60-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 0.75h;	To a mixture of phenyl ethylenediamine (3.0 g, 22.12 mmol), DIPEA (4.65 mL, 26.54 mmol) and DCM (25 mL) was added slowly with stirring and ice-bath cooling a solution of 9-fluorenylmethyl chloroformate (5.72 g, 22.12 mmol) in methylene chloride (25 mL) under argon for a period of 30 min, the reaction mixture was stirred further at room temperature for 15 min. The reaction mixture was then washed with 1N HCL (15 mL), followed by 10% NaHCO3(15 mL) and brine (15 mL), dried (Na2SO4) and concentrated to give 7.8 g of crude compound which was crystallized from ethyl acetate to give 6.5 g (82%) of pure product as white solid; mp. 174-175C. Rf = 0.54 (1:2 EtOAc/Pentane) 1H NMR (200 MHz, DMSO-d6) delta (ppm) 7.87 (d, J = 7.24 Hz, 2H), 7.67 (m, 3H), 7.27-7.43 (m, 9H), 4.2-4.31 (m, 3H), 3.31 (bs, 4H). 13C NMR (200 MHz, DMSO-d6) delta (ppm) 156.07, 143.74, 140.66, 138.6, 138.18, 129.63, 127.58, 127.03, 125.16, 121.09, 120.06, 65.56, 48.46, 46.6, 36.97.

Reference： [1]Patent: EP1826199,2007,A1 .Location in patent: Page/Page column 57; 64
[2]Journal of Organic Chemistry,2010,vol. 75,p. 2492 - 2500

21
[ 10397-13-4 ]
[ 1664-40-0 ]
[ 944402-01-1 ]

Yield	Reaction Conditions	Operation in experiment
96%		[0410] To a solution of <strong>[10397-13-4]4-(4,6-dichloropyrimidin-2-yl)morpholine</strong> (prepared as described in Method 22; 932 mg, 4.0 mmol) and DEEA (0.7 mL, 4.0 mmol) in ACN (4O mL), neat N^phenyl-ethane-l^-diamine (0.523 mL, 4.0 mmol) was slowly added. The reaction mixture was stirred at 70-800C under nitrogen. After 20 hours, the reaction mixture was cooled down, and the solvent was removed under reduced pressure. The crude product was partitioned between EtOAc (12O mL) and 0.1 M NaHCOa (5O mL). The organic layer was washed with additional 0.1 M NaHCO3 (2x50 mL), brine (50 mL), dried, filtered and concentrated to give ^-(-chloro^-morpholinopyrimidin^-y^-iV2- phenylethane-l,2-diamine, as an off-white solid (1.29 g, 96%). LC/MS (m/z): 334.0 (MH+), Rt 1.94 minutes.

Reference： [1]Patent: WO2007/84786,2007,A1 .Location in patent: Page/Page column 147-148

22
[ 576-83-0 ]
[ 1664-40-0 ]
[ 1000298-75-8 ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 8082 - 8085
[2]Chemistry - A European Journal,2009,vol. 15,p. 9451 - 9457

23
[ 1121-60-4 ]
[ 1664-40-0 ]
[ 62402-17-9 ]

Yield	Reaction Conditions	Operation in experiment
74%		General procedure: The ligand was synthesized using the reported procedure [52]. To N-methylethylenediamine (0.74 g, 10 mmol) in methanol (20 mL) was added dropwise pyridine-2-carboxaldehyde (1.10 g, 10 mmol) in methanol (20 mL). The mixture was stirred overnight to get a bright yellow solution. To this was added NaBH4 (0.57 g, 15 mmol), the solution stirred for another day and then rotaevaporated to dryness. The resulting solid was dissolved in water and the organic layer was extracted with CH2Cl2 and dried with anhydrous sodium sulphate. The CH2Cl2 layer was rotaevaporated to get N-methyl-N?-(pyrid-2-ylmethyl) ethylenediamineas an yellow oil. The yield was 1.15 g (70%)

Reference： [1]Tetrahedron,2008,vol. 64,p. 4011 - 4025
[2]Inorganica Chimica Acta,2019,vol. 485,p. 98 - 111

24
[ 888410-75-1 ]
[ 1664-40-0 ]
[ 1027754-40-0 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 4011 - 4025

25
[ 64-17-5 ]
[ 1664-40-0 ]
[ 380151-85-9 ]
1-phenyl-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]imidazolidine*0.5ethanol [ No CAS ]

Reference： [1]New Journal of Chemistry,2003,vol. 27,p. 1419 - 1424

26
[ 139756-22-2 ]
[ 1664-40-0 ]
[ 1007310-81-7 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 2807 - 2815

27
[ 7154-73-6 ]
[ 27578-60-5 ]
[ 140-31-8 ]
[ 2038-03-1 ]
[ 25560-00-3 ]
[ 123-00-2 ]
[ 5036-48-6 ]
[ 7663-77-6 ]
[ 34035-03-5 ]
[ 1761-71-3 ]
[ 6864-37-5 ]
[ 2213-43-6 ]
[ 63234-71-9 ]
[ 5906-35-4 ]
[ 59983-39-0 ]
[ 1664-40-0 ]
[ 6530-09-2 ]
[ 108-00-9 ]
[ 109-55-7 ]
[ 51387-90-7 ]
[ 102-83-0 ]
[ 849908-66-3 ]
C₁₅H₁₇ClN₂O [ No CAS ]
[ 849908-70-9 ]
[ 940358-24-7 ]
C₁₆H₁₉ClN₂O [ No CAS ]
C₁₉H₁₉ClN₂O [ No CAS ]
[ 849908-71-0 ]
C₁₇H₂₁ClN₂O₂ [ No CAS ]
[ 849908-67-4 ]
C₁₇H₂₁ClN₂O [ No CAS ]
[ 880815-24-7 ]
C₁₇H₂₂ClN₃O [ No CAS ]
C₁₈H₂₁ClN₂O [ No CAS ]
[ 849908-65-2 ]
[ 932172-19-5 ]
[ 875001-79-9 ]
[ 849908-68-5 ]
[ 849908-69-6 ]
[ 849908-81-2 ]
[ 849908-75-4 ]

Yield	Reaction Conditions	Operation in experiment
	With polymer-bound trimethyl ammonium cyanoborohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃; for 24 - 36h;Combinatorial reaction / High throughput screening (HTS);	All sixty diamines were separated in four groups based on their steric and electronic characteristics, Figures 1-4. Each diamine was measured in the amount of 0.05 g (approximately 0.3 mmol) and pooled together with the others in the group. Obtained diamine mixtures were dissolved in 5 ml of 1,2-dichloroethane and used for the syntheses. Each well of the 96-well filterplates was loaded with 0.2 ml of 1: 10 mixture of acetic acid: DCE, 0.03 ml of the diamine mixture in DCE (group 1, group 2, group 3, or group 4) to assure 0.04 mmol of the diamines per well, and shaken for 5 min at room temperature. Appropriate carbonyl compounds from the master plate (0.1 ml of 1.2 M solution) were added into corresponding wells of the reaction plates followed by the addition of (polystyrylmethyl) trimethylammonium cyanoborohydride, (0.020 g, 0.08 mmol per well). The reaction plates were sealed and placed on a shaker. The reaction was allowed to proceed 24-36 hours at room temperature. At the end, the reaction mixtures were filtered using a filtration manifold, and products were collected into four (one per group) collection plates. Solvents were evaporated in SpeedVac and formed residues were analyzed by mass spectrometry prior to biological screening. Mono and double alkylated products were observed in 1: 0.5 to 1: 2 ratios by mass spectral analysis.

Reference： [1]Patent: WO2005/34857,2005,A2 .Location in patent: Page/Page column 15; 22

28
[ 105640-07-1 ]
[ 1664-40-0 ]
[ 110-16-7 ]
trans-4-[4-(2-phenylaminoethylamino)cyclohexyl]phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%	Stage #1: 4-(4-hydroxyphenyl)cyclohexan-1-one; N-(2-aminoethyl)benzeneamine In tetrahydrofuran; isopropyl alcohol for 3h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; isopropyl alcohol Stage #3: maleic acid In methanol; diethyl ether	25 EXAMPLE 25; Trans-4-[4-(2-phenylaminoethylamino)Cyclohexyl]Phenol EXAMPLE 25 trans-4-[4-(2-phenylaminoethylamino)Cyclohexyl]Phenol To a stirred solution of 4-(4-hydroxyphenyl)cyclohexanone (1.0 g, 5.3 mmol) in a mixture of 2-propanol (40 ML) and THF (20 ML) was added N -phenylethylenediamine (0.72 g, 5.3 mmol) and 3Å molecular sieves.After 3 hours, sodium borohydride (0.27 g, 7.3 mmol) was added, and the reaction mixture was stirred overnight.The reaction mixture was quenched with MeOH, filtered through celite, and the filtrate was concentrated under reduced pressure.The product was purified by flash chromatography (silica, 95:5 CH2Cl2:MeOH) and converted to a maleate salt.Recrystallization from MeOH/Et2O gave trans-4-[4-(2-phenylamino-ethylamino)cyclohexyl]phenol (0.31 g, 14%), as yellow solid: mp 180-184° C.; IR (KBr): 3368, 2945, 2863, 1516 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 9.14 (s, 1H), 8.40 (br s, 2H), 7.15-7.00 (m, 4H), 6.70-6.55 (m, 5H), 6.02 (s, 2H), 5.65 (br s, 1H), 3.40-3.25 (m, 2H), 3.20-3.10 (m, 3H), 2.45-2.40 (m, 1H), 2.20-2.10 (m, 2H), 1.90-1.80 (m, 2H), 1.50-1.35 (m, 4H); API-MS (m/z): 311 [M+H]+; HPLC: method A, 7.38 minutes (99.1%); method B, 13.29 minutes (99.1%); Anal. Calcd for C20H26N2O.C4H4O4: C, 67.59; H, 7.09; N, 6.57. Found: C, 67.38; H, 7.01; N 6.55.

Reference： [1]Current Patent Assignee: PFIZER INC - US2003/236286, 2003, A1 Location in patent: Page 20

29
[ 640-60-8 ]
[ 1664-40-0 ]
[ 150-61-8 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 13848 - 13849

30
[ 1664-40-0 ]
[ 6160-65-2 ]
[ 16099-65-3 ]

Yield	Reaction Conditions	Operation in experiment
35.3%	In tetrahydrofuran; at 20℃; for 2h;	Example 191; N-(3-fluoro-4-(2-(5-((2-methoxyethylamino)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7- yloxy)phenyl)-3-phenyl-2-thioxoimidazolidine- 1 -carboxamide (303); Step 1. 1-phenylimidazolidine-2-thione (301); l,l'-Thiocarbonyldiimidazole (4.51 g, 25.3 mmol) was added to a solution of N- phenylethylenediamine (3 mL, 23.02 mmol) in THF (230 mL) and the mixture was stirred for 2h at room temperature. DCM was added and the solution was washed with 1N HCl, dried over anhydrous sodium sulfate and concentrated under reduced pressure affording title compound 301 (1.45 g, 8.13 mmol, 35.3 % yield), m/z: 179.1 (M+H)+

Reference： [1]Chemical Science,2019,vol. 10,p. 6539 - 6552
[2]Patent: WO2009/26717,2009,A1 .Location in patent: Page/Page column 144-145

31
[ 906087-84-1 ]
[ 1664-40-0 ]
[ 906086-33-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 3h;	Example 398 N-(3-(((2-anilinoethyl)amino)carbonyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)pyridine-2-carboxamide To a solution of 4-((pyridin-2-ylcarbonyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylic acid obtained in Reference Example 54 (0.63 g, 2.0 mmol) and <strong>[1664-40-0]N-phenylethylenediamine</strong> (0.31 mL, 2.4 mmol) in DMF (10 mL), WSC (0.41 g, 2.4 mmol), HOBt (0.32 g, 2.4 mmol) and triethylamine (0.33 mL, 2.4 mmol) were added, and the mixture was stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, passed through a small amount of silica gel and evaporated under reduced pressure. Diethyl ether was added to the precipitated crystals, and the crystals were collected by filtration to give the title compound (0.69 g, yield 79%) as crystals. melting point 182-183 C. 1H-NMR (CDCl3): delta 1.55-1.80 (3H, m), 1.95-2.15 (2H, m), 2.15-2.30 (1H, m), 3.35-3.50 (2H, m), 3.65-3.80 (3H, m), 4.00-4.15 (2H, m), 5.35 (1H, dd, J=9.6 Hz), 6.66 (2H, d, J=8.4 Hz), 6.72 (1H, t, J=7.2 Hz), 7.10-7.30 (3H, m), 7.40-7.50 (1H, m), 7.88 (1H, td, J=7.5, 1.5 Hz), 8.24 (1H, d, J=7.8 Hz), 8.58 (1H, s), 8.75 (1H, d, J=4.5 Hz), 11.69 (1H, s).

Reference： [1]Patent: US2009/156582,2009,A1 .Location in patent: Page/Page column 64

32
[ 1664-40-0 ]
[ 4887-95-0 ]
N₁-(6-chloro-1H-benzo[d]imidazol-2-yl)-N₂-phenylethane-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine at 110℃;	83 Example 83 A neat mixture of 2,5-dichloro-1 H-benzoimidazole (150 mg, 0602 mmol), N- phenyl ethylenediamine (110 mg, 0.808 mmol, 1 eq) and N,N-diisopropylethyl amine (210 mL, 1.21 mmol, 1.5 eq.) in sealed tube was heated overnight at 1100C. The mixture was directly loaded onto a silica gel column and eluted with 5% methanol in dichloromethane to provide 144 mg of N1-(6-chlora-1 H- benzo[d]imidazol-2-yl)-N2-phenylethane-1 ,2-diamine.

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/143039, 2009, A2 Location in patent: Page/Page column 137

33
[ 1670-83-3 ]
[ 939-97-9 ]
[ 1664-40-0 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-(2-phenylamino-ethyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%		Example 91; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-(2-phenylamino-ethyl)-amide 85; 81 mg (0.5 mmol) of 4-tert-butyl benzaldehyde and 68 mg (0.5 mmol) of N-phenyl ethyl-ene diamine were dissolved in 2 ml methanol and the solution was stirred for 2 h at rt. 18.5 mg (0.5 mmol) of sodium borohydride were added in portions under nitrogen. The reaction mixture was stirred at rt for 30 min, the solvent was evaporated and the residue was suspended in 4 ml DCM. 88 mg (0.55 mol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 105 mg (0.55 mmol) of EDC.HCl were added and the mixture was stirred at rt over night. The product was purified by column chromatography (silica gel; diethyl ether) to yield 80 mg (37%) product as a colorless oil. MS (ISP) 426.5 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 74

34
[ 875340-09-3 ]
[ 1664-40-0 ]
[ 7693-46-1 ]
C₂₆H₂₃FN₆O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 118; N-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-3-phenyl-2-thioxoimidazolidine-1-carboxamide (286); To a mixture of 12 (150 mg, 0.44 mmol) and DIPEA (0.084 mL, 0.48 mmol) in THF (4.5 mL) 4-nitrophenyl carbamate (97 mg, 0.48 mmol) was added and the mixture stirred 30 min at room temperature. Thereafter N'-phenylethane-1,2-diamine (0.086 mL, 0.66 mmol) was added and the mixture was stirred for 1 h more, to form the intermediate 287 (not isolated). Thiophosgene (0.05 mL, 0.66 mmol) and DIPEA (0.232 mL, 1.38 mmol) were added and the mixture was stirred overnight at room temperature. More thiophosgene (0.05 mL, 0.66 mmol) was added and the mixture was heated to reflux for 3 h more. The mixture was diluted with DCM, extracted with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (5% MeOH in DCM) followed by trituration of the resulting solid with MeOH affording title compound 286 (61 mg, 0.11 mmol, 25%) as a cream solid. 1H NMR (400 MHz, DMSO-d6) delta (ppm): 12.56(s, 1H), 8.45(d, J=5.5 Hz, 1H), 7.87(d, J=1.2 Hz, 1H), 7.82(dd, J=2.5 Hz, J=12.7 Hz, 1H), 7.73(d, J=0.8 Hz, 1H), 7.67(s, 1H), 7.52-7.48(m, 5H), 7.42-7.35(m, 2H), 6.31(dd, J=5.5 Hz, J=0.8 Hz, 1H), 4.27-4.22(m, 2H), 4.13-4.09(m, 2H), 3.73(s, 3H). MS (m/z): (M+1) 545.2 (100%).

Reference： [1]Patent: US2007/4675,2007,A1 .Location in patent: Page/Page column 145-146

35
[ 1196103-81-7 ]
[ 1664-40-0 ]
[ 1315564-88-5 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h;	Synthesis of 2-(4-Chloro-benzenesulfonyl)-2-methyl-N-(2-phenylamino-ethyl)- propionamide (Example 19, Table 4)Activation of 100 mg (0.38 mmol) of 2-(4-chloro-benzenesulfonyl)-2-methyl-propionic acid as the corresponding acid chloride is achieved by treatment with thionyl chloride (2 mL) at 80 C for 2 h. The reaction is cooled to room temperature and excess thionyl chloride is removed under reduced pressure. The crude acidchloride is dissolved in DCM (1 mL) and added dropwise to a solution of <strong>[1664-40-0]N-phenylethylenediamine</strong> (52 mg, 0.38 mmol) and N,N- diisopropylethylamine (66 mu, 0.38 mmol) in DCM (1 mL). The reaction is stirred at room temperature for 16 h. The reaction mixture is washed with saturated aqueous NaHC03 solution. The organic layer is separated, dried (Na2S04), filtered and the filtrate isconcentrated under reduced pressure. The residue is purified by column chromatography (silica, eluent: DCM, ethyl acetate) to give 110 mg of example 19. Yield: 76%; ES-MS: m/z 381 [M+H]

Reference： [1]Patent: WO2011/88015,2011,A1 .Location in patent: Page/Page column 48

36
[ 32315-10-9 ]
[ 1664-40-0 ]
[ 1848-69-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine; In tetrahydrofuran; at 0℃; for 0.583333h;	Step iii: Compound 84 was also synthesized using method described by Neville. Briefly, triphosgene ( 12.2 mmol) was dissolved in 40 mL of tetrahydrofuran and cooled at 0C. To the resulting solution was added (36.7 mmol) of N-phenylethylenediamine dissolved in 65 mL of tetrahydrofuran and 7.7 mL of triethylamine over a period of 30 min. White solid immediately precipitated. The reaction was complete after 5 min. The reaction mixture was quenched with water and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (methylene chloride to methylene chloride/ethyl acetate 3: 10) to afford a white solid.; Example 11984C9H10N2OExact Mass: 162,07931[00208] l-Phenylimidazolidin-2-one (84). Yield: 98%; Compound 84 was also synthesized using method described by Neville. Briefly, triphosgene (12.2 mmol) was dissolved in 40 mL of tetrahydrofuran and cooled at 0C. To the resulting solution was added (36.7 mmol) of N- phemiethjienediamine dissolved in 65 mL of tetrahydrofuran and 7.7 mL of trietlrylamine over a period of 30 min. White solid immediately precipitated. The reaction was complete after 5 min. The reaction mixture was quenched with water and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (methylene chloride to methylene chloride/ethyl acetate 3: 10) to afford a white solid. Yield: 80%; mp: 154-156 C; IR v: 3240, 1680 cm"1: NMR (DMSO-d6): delta 7.58-7.55 (m, 2H, Ar), 7.34-7.29 (m, 2H, Ar), 7.02-6.95 (m, 2H, Ar and NH), 3.88-3.83 (m, 2H, CH2), 3.44-3.39 (m, 2H,
80%	With triethylamine; In tetrahydrofuran; at 0℃; for 0.5h;	Sodium hydride (3 eq.) was slowly added to a cold solution of compound 49 (1 eq.) in tetrahydrofuran under dry nitrogen atmosphere. The ice bath was removed after 30 min and the reaction mixture was stirred at room temperature for 5 h. The reaction was quenched at 0 C with water and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 50, which were used without further purification to afford white solids. Yield: 98%; Compound 50 was also synthesized using method described by Neville refPreviewPlaceHolder[40]. Briefly, triphosgene (12.2 mmol) was dissolved in 40 mL of tetrahydrofuran and cooled at 0 C. To the resulting solution was added (36.7 mmol) of N-phenylethylenediamine dissolved in 65 mL of tetrahydrofuran and 7.7 mL of triethylamine over a period of 30 min. A white solid immediately precipitated and the reaction was complete after 5 min. The reaction mixture was quenched with water and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (CH2Cl2 to CH2Cl2/AcOEt 3:10) to afford a white solid. Yield: 80%; mp: 154-156 C; IR nu: 3240, 1680 cm-1; 1H NMR (DMSO-d6): delta 7.58-7.55 (m, 2H, Ar), 7.34-7.29 (m, 2H, Ar), 7.02-6.95 (m, 2H, Ar and NH), 3.88-3.83 (m, 2H, CH2), 3.44-3.39 (m, 2H, CH2); 13C NMR (CDCl3): delta 160.2, 140.2, 128.8, 122.7, 117.9, 45.3, 37.5.
	With triethylamine; In tetrahydrofuran; at 0℃; for 0.583333h;	Compound 1 was also prepared using a method described by Neville. Briefly, triphosgene (12.2 mmol) was dissolved in 40 ml_ of dry tetrahydrofuran and cooled at 0C. /V-phenylethylenediamine (36.7 mmol) dissolved in 65 mL of tetrahydrofuran and 7.7 ml_ of triethylamine was added over a period of 30 min to the triphosgene solution. A white solid immediately precipitated and the reaction was complete after 5 min. The reaction mixture was quenched with water and diluted with ethyl acetate. The organic layer was washed with water, brine and dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (methylene chloride to methylene chloride/ethyl acetate 3:10) to afford a white solid.

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4559 - 4580
[2]Patent: WO2011/100840,2011,A1 .Location in patent: Page/Page column 25; 84-85
[3]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5327 - 5342
[4]Patent: WO2013/23274,2013,A1 .Location in patent: Paragraph 0070

37
[ 6959-47-3 ]
[ 1664-40-0 ]
[ 1333877-94-3 ]

Yield	Reaction Conditions	Operation in experiment
69%		A solution of 2-bromoethylamine hydrobromide (1.1 g, 5.4 mmol) and aniline (3.0 g, 32 mmol) in toluene (8 ml) was stirred for 1 day at 120 C under an argon atmosphere and the precipitated product was collected by filtration. The salt was then treated with a 20% aqueous NaOH solution and extracted with dichloromethane. The organic phase was dried over anhydrous Na2SO4. After the Na2SO4 was filtered out and the solvent was distilled the crude product was further purified by column chromatography on silica gel (eluant: methanol) to afford <strong>[1664-40-0]N-phenylethylenediamine</strong> as a red-brown liquid. Yield: 87% (0.64 g); 2-(Chloromethyl)pyridine hydrochloride (1.8 g, 11 mmol) was treated with a 20% aqueous NaOH solution and extracted with dichloromethane and the organic phase was dried over anhydrous Na2SO4. After Na2SO4 was filtered out and the solvent was evaporated off, a solution of 2-(chloromethyl)pyridine in benzene (3 ml) was added to a solution of <strong>[1664-40-0]N-phenylethylenediamine</strong> (0.69 g, 5.1 mmol), which was prepared as described above, and triethylamine (5.1 g, 51 mmol) in benzene (4 ml) and stirred for 17 h at 80 C under an argon atmosphere. After being cooled to room temperature and the addition of diethyl ether, the inorganic by-products were removed by washing with a saturated NaHCO3 solution and with brine. The organic phase was dried over anhydrous Na2SO4. After the Na2SO4 was filtered out and the solvent was removed the crude product was purified by column chromatography on silica gel (eluant: ethyl acetate) to afford 2a as a red-brown viscous liquid. Yield: 69% (1.1 g); 1H NMR (400 MHz, CDCl3) delta 2.86 (t, 2H), 3.17 (t, 2H), 3.88 (s, 4H), 6.58 (d, 2H), 6.65 (t, 1H), 7.07-7.18 (m, 4H), 7.41 (d, 2H), 7.60 (t, 2H), 8.54 (d, 2H); 13C NMR (100 MHz, CDCl3) delta 41.80, 53.26, 60.73, 113.22, 117.34, 122.50, 123.54, 129.53, 136.84, 149.04, 149.53, 159.66; HRMS (EI): calcd for C20H22N4: 318.1844. Found: 318.1846.

Reference： [1]Tetrahedron,2011,vol. 67,p. 6927 - 6933

38
[ 31010-60-3 ]
[ 1664-40-0 ]
[ 1337912-77-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	In methanol; at 60℃;Sealed tube;	General procedure: To a suspension of 50 mg (0.23 mmol) 3 in 2 mL MeOH in a sealed conical vial was added 0.3 mL methylamine. This was stirred overnight at 60 C resulting in a homogeneous yellow solution, at which point the reaction was complete by LCMS. Addition of 1 mL THF resulted in product precipitation. The yellow solid was filtered off and washed with cold methanol followed by THF, then dried under vacuum to give 42.3 mg (85% yield) 9.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3608 - 3615

39
[ 1664-40-0 ]
[ 380151-85-9 ]
[ 637340-84-2 ]

Reference： [1]New Journal of Chemistry,2003,vol. 27,p. 1419 - 1424

40
[ 1664-40-0 ]
[ 79-22-1 ]
[ 79143-47-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In water; ethyl acetate; at 20℃; for 2h;Cooling with ice;	Reference Example 17-1; To a solution of Compound 1 (1.36 g) in ethyl acetate (17 ml) were added 10% sodium bicarbonate water (16.8 ml) and methyl chloroformate (1.08 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 2 hours, and then separated. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent n-hexane-ethyl acetate 3:2) to give Compound 2 (1.00 g) as a yellow oily substance.MS (APCI) 195 [M+H]+

Reference： [1]Patent: US2012/16117,2012,A1 .Location in patent: Page/Page column 40

41
[ 591-50-4 ]
[ 107-15-3 ]
[ 1664-40-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With aluminum oxide; copper; potassium hydroxide; for 0.25h;	General procedure: Iodobenzene (1 mmol), ethanolamine (3 mmol), KOH (3.7 mmol) and Cu0 powder (1 mmol, 63 mg) werestirred for different times (15 min, 25 min, 30 min, 1 hr, 2 hrs, 3 hrs, 4 hrs, 1 day, 2 days). The crudeproduct was dissolved in CH2Cl2 (2 mL) and filtered on Buechner funnel with a sintered glass disc usingCH2Cl2. The solvent was evaporated in vacuum, the crude product was dried and analyzed by GC-MS. Themixture was purified by flash chromatography on silica gel (CH2Cl2-methanol-ammonia) to afford thedesired product. The pure product was analyzed by 1H, 13C NMR spectroscopy and MALDI-TOF massspectrometry after dissolution in an appropriate solvent. Milling was accomplished with 10 mmol of diethylamine. 1H NMR(300 MHz, CDCl3): delta 7.13 (2 H, t, J = 6 Hz), 6.65 (1 H, t, J = 9 Hz), 6.67 (2 H, d, J = 3 Hz), 3.82 (2 H, t, J= 3Hz), 3.29 (2H, br s). ppm; 13C NMR (75 MHz, CDCl3): delta 148.8, 129.7, 117.8, 113.4, 46.8, 41.5 ppm. 1HNMR (300 MHz, CDCl3) and 13C NMR (75 MHz, CDCl3) were in accordance with the reported values inliterature [3] m/z (MALDI-TOF MS): calcd for C8H12N2 [M + H]+: 137.1000, found: 137.1001
99%	With copper(l) chloride; potassium hydroxide; at 0 - 20℃;	CuCl (265 mg, 2.7 mmol),KOH (3.01 g, 53 mmol),And iodobenzene (3.00 mL, 27 mmol) in dichloromethaneEthylenediamine (5.38 mL, 80 mmol) was slowly added at 0 C.After stirring overnight at room temperature, the reaction mixture was diluted with water (30 mL), washed with CH 2 Cl 2 (20 mL × 5).The combined organic layers were dried over Na 2 SO 4, filtered and concentrated in vacuo to afford the desired compound as a brown oil (3.63 g, 99%)
99%	With copper(l) chloride; potassium hydroxide; at 0 - 20℃;Inert atmosphere;	To a suspension ofCuCl (265 mg, 2.7 mmol), KOH (3.01 g, 53 mmol) and iodobenzene(4a: 3.00 mL, 27 mmol) was slowly added ethylenediamine (5:5.38 mL, 80 mmol) at 0 C. After being stirred overnight at roomtemperature, the reaction mixture was diluted with water (30mL) and extracted with CH2Cl2 (20 mL 5). The combined organiclayers were dried over Na2SO4, filtered off and concentrated invacuo to give 6a (3.63 g, 99% yield) as a brown oil. 1H NMR (400MHz, CDCl3) d 7.18 (t, J = 7.6 Hz, 2H), 6.71 (t, J = 7.6 Hz, 1H), 6.64(d, J = 7.6 Hz, 2H), 4.01 (brs, 1H), 3.19 (t, J = 5.6 Hz, 2H), 2.95 (t, J= 6.4 Hz, 2H), 1.50 (brs, 2H); 13C NMR (150 MHz, CDCl3) d 148.4,129.3, 117.4, 113.0, 46.5, 41.2.

98%	With copper(l) chloride; potassium hydroxide; at 0℃; for 8h;Neat (no solvent);	General Procedure: CuCl (10 mg, 0.1 mmol), aryl iodided (if solid, 1.0 mmol), and KOH (112 mg, 2.0 mmol) were added to a screw-capped test tube. Aryl iodided (if liquid, 1.0 mmol), and dimine (3 mmol) were added by syringe. The reaction mixture was stirred at 0C for 8h. The resulting mixture was diluted with water (2 mL) before extraction with methylene chloride (4×10 mL), and dried over Na2SO4, the filtrate was concentrated under reduced pressure, and the mixture was purified by column chromatography on silica gel to afford the desired product.
94%	With chitosan Cu2+ complex; In acetonitrile; for 3h;Reflux; Green chemistry;Catalytic behavior;	General procedure: Aryl halide (1.0 equiv) and aliphatic diamines/amino alcohol (2.0 equiv) were taken in a 100 ml round bottom flask along with 100-150 mg of the chitosan copper catalyst in CH3CN (15 ml) solvent. The resultant mixture was heated at reflux for 3-6 h. After completion of the reaction (the complete consumption of starting materials was confirmed by TLC) the reaction mixture was extracted with ethylacetate. The separated organic phase was concentrated to get the gummy liquid product 3. The chitosan copper catalyst was collected by simple decanting off the reaction mixture. The recovered catalyst was then washed thoroughly with ethyl acetate 2-3 times,dried under vacuum at 50C and used for another run.
89.9%	With copper(l) iodide; potassium hydroxide; at 0℃; for 10h;	CuI (0.1 mmol), and KOH (2.0 mmol) were added to a solution of aryl iodide (if solid, 1.0 mmol), and ethylenedimine (3 mmol) reaction mixture. Further, the resulting reaction mixture was stirred at 00C for 10h. After that the obtained resulting mixture was diluted with water (2 mL) and extraction with dichloromethane three times (40 mL). Further, the solution was evaporated under reduced pressure, and the obtained crude product was purified by column chromatography on silica gel using eluent 7:3 hexane-ethyl acetate mixture to afford the colourless liquid product. (yield: 89.9%). 1H NMR (400 MHz, CDCl3) delta 8.65 (d, J = 8.0 Hz, 1H), 8.55 (d, J = 8.0 Hz, 1H), 8.40 (d, J = 8.0 Hz, 1H), 8.03 (d, J = 8.0 Hz, 1H), 7.85 (t, J = 8.0 Hz, 1H), 4.15 (t, J = 7.2 Hz, 2H), 1.80 (m, 2H), 1.06 (br, 4H).13C NMR (CDCl3): delta 131.8, 131.7, 131.1, 130.0, 129.7, 128.9, 123.0, 119.6, 115.5, 115.1, 113.6, 112.7, 111.5, 108.6, 108.2,106.7, 45.44. MS (HRMS): m/z calcd for C8H12N2 [M+H]+ 388.0967, found 388.1046.
87%	With potassium hydroxide; In dimethyl sulfoxide; at 100℃; for 5h;	General procedure: A mixture of aryl halide (1.0 mmol), Het-NH (1.2mmol) or amine (4 mmol), KOH (2 mmol), Cu2O/nano-CuFe2O4 magnetic composite (0.010 g) and anhydrous DMSO (2 mL) was stirred at 100 C. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to room temperature and with diluted ethyl acetate and the catalyst was separated by an external magnet from the mixture, washed with acetone, dried in an oven at 80 C for 3 h and re-used for a consecutive run under the same reaction conditions. The combined ethyl acetate layer was washed with water, dried over anhydrous MgSO4, The residue was purified by recrystallization or short column chromatography on silica gel to afford the target products in excellent yield.
82.5%	With copper(l) chloride; potassium hydroxide; at 25℃; for 12h;	Using (11a) of the preparation method, to obtain light yellow liquid, yield 82.5%.
80%	With copper(II) oxide; In acetonitrile; for 48h;Reflux; Inert atmosphere;	General procedure: In a 10 mL flask were placed aryl halide (0.5 mmol), diamine (1.0; 2.0 or 3.7 mmol), copper catalyst (0.5; 1.0 or 10 mol %), and acetonitrile (2-3 mL). The reaction was then kept under stirring and reflux. After the reaction was complete (TLC), the resulting mixture was diluted with brine (2-3 mL) and extracted with ethyl acetate (4 Chi 7 mL). Then the organic phase was dried over anhydrous sodium sulfate, filtered under Celite, and the solvent was eliminated by vacuum. The crude product was then analyzed by 1H NMR. When necessary, the mixture was purified by column chromatography on silica gel or by thin layer chromatography plates with UV 254 nm to afford the desired product.

Reference： [1]Synlett,2015,vol. 26,p. 2789 - 2794
[2]Patent: JP2017/178811,2017,A .Location in patent: Paragraph 0185-0190
[3]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 775 - 785
[4]Tetrahedron Letters,2012,vol. 53,p. 1265 - 1270
[5]Tetrahedron Letters,2015,vol. 56,p. 419 - 424
[6]Tetrahedron Letters,2018,vol. 59,p. 3858 - 3862
[7]Chemistry Letters,2016,vol. 45,p. 223 - 225
[8]Patent: CN105541777,2016,A .Location in patent: Paragraph 0016; 0074; 0075; 0076
[9]Tetrahedron Letters,2013,vol. 54,p. 2332 - 2335

42
[ 1664-40-0 ]
[ 142770-42-1 ]
[ 1351934-60-5 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

43
[ 381-73-7 ]
[ 1664-40-0 ]
[ 1069085-50-2 ]

Yield	Reaction Conditions	Operation in experiment
77%	With tetrachloromethane; triethylamine; triphenylphosphine; at 0℃; for 18h;Reflux; Inert atmosphere;	General procedure: A 200-mL three-necked flask equipped with a condenser was charged with Ph3P (34.5 g, 132mmol), Et3N (excess), CCl4 (21.1 ml, 220 mmol), and the fluorinated carboxylic acid (44 mmol) at 0 C under nitrogen. After the solution was stirred for about 10 min (ice water bath), thenN-substituted alkyl diamine or 2-amino-3-phenyl propanol (53 mmol) dissolved in CCl4 (21.1 ml, 220 mmol) was added. The mixture was refluxed under stirring for 3-18 h. Solvent was evaporatedunder reduced pressure, and the residue was diluted with petroleum ether (60-90 C) and filtered.The residual solid of Ph3PO and Et3N*HCl was washed with petroleum ether 3 times. The filtratewas concentrated, and the residue was then purified by column chromatography to offer the product 3. When N-benzylethylenediamine and <strong>[1664-40-0]N-phenylethylenediamine</strong> were employed, imidoyl chloride2b, 2f, 2g, 2m can be isolated by shorting the stirring time to 1-2 h.

Reference： [1]Tetrahedron,2012,vol. 68,p. 2858 - 2863

44
[ 375-22-4 ]
[ 1664-40-0 ]
[ 1069085-53-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrachloromethane; triethylamine; triphenylphosphine; at 0℃; for 18h;Reflux; Inert atmosphere;	General procedure: A 200-mL three-necked flask equipped with a condenser was charged with Ph3P (34.5 g, 132mmol), Et3N (excess), CCl4 (21.1 ml, 220 mmol), and the fluorinated carboxylic acid (44 mmol) at 0 C under nitrogen. After the solution was stirred for about 10 min (ice water bath), thenN-substituted alkyl diamine or 2-amino-3-phenyl propanol (53 mmol) dissolved in CCl4 (21.1 ml, 220 mmol) was added. The mixture was refluxed under stirring for 3-18 h. Solvent was evaporatedunder reduced pressure, and the residue was diluted with petroleum ether (60-90 C) and filtered.The residual solid of Ph3PO and Et3N*HCl was washed with petroleum ether 3 times. The filtratewas concentrated, and the residue was then purified by column chromatography to offer the product 3. When N-benzylethylenediamine and <strong>[1664-40-0]N-phenylethylenediamine</strong> were employed, imidoyl chloride2b, 2f, 2g, 2m can be isolated by shorting the stirring time to 1-2 h.

Reference： [1]Tetrahedron,2012,vol. 68,p. 2858 - 2863

45
[ 354-08-5 ]
[ 1664-40-0 ]
N-phenyl-2-bromodifluoromethylimidazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With tetrachloromethane; triethylamine; triphenylphosphine; at 0℃; for 18h;Reflux; Inert atmosphere;	General procedure: A 200-mL three-necked flask equipped with a condenser was charged with Ph3P (34.5 g, 132mmol), Et3N (excess), CCl4 (21.1 ml, 220 mmol), and the fluorinated carboxylic acid (44 mmol) at 0 C under nitrogen. After the solution was stirred for about 10 min (ice water bath), thenN-substituted alkyl diamine or 2-amino-3-phenyl propanol (53 mmol) dissolved in CCl4 (21.1 ml, 220 mmol) was added. The mixture was refluxed under stirring for 3-18 h. Solvent was evaporatedunder reduced pressure, and the residue was diluted with petroleum ether (60-90 C) and filtered.The residual solid of Ph3PO and Et3N*HCl was washed with petroleum ether 3 times. The filtratewas concentrated, and the residue was then purified by column chromatography to offer the product 3. When N-benzylethylenediamine and N-phenylethylenediamine were employed, imidoyl chloride2b, 2f, 2g, 2m can be isolated by shorting the stirring time to 1-2 h.

Reference： [1]Tetrahedron,2012,vol. 68,p. 2858 - 2863

46
[ 1664-40-0 ]
[ 76-05-1 ]
[ 1069085-41-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrachloromethane; triethylamine; triphenylphosphine; at 0℃; for 18h;Reflux; Inert atmosphere;	General procedure: A 200-mL three-necked flask equipped with a condenser was charged with Ph3P (34.5 g, 132mmol), Et3N (excess), CCl4 (21.1 ml, 220 mmol), and the fluorinated carboxylic acid (44 mmol) at 0 C under nitrogen. After the solution was stirred for about 10 min (ice water bath), thenN-substituted alkyl diamine or 2-amino-3-phenyl propanol (53 mmol) dissolved in CCl4 (21.1 ml, 220 mmol) was added. The mixture was refluxed under stirring for 3-18 h. Solvent was evaporatedunder reduced pressure, and the residue was diluted with petroleum ether (60-90 C) and filtered.The residual solid of Ph3PO and Et3N*HCl was washed with petroleum ether 3 times. The filtratewas concentrated, and the residue was then purified by column chromatography to offer the product 3. When N-benzylethylenediamine and <strong>[1664-40-0]N-phenylethylenediamine</strong> were employed, imidoyl chloride2b, 2f, 2g, 2m can be isolated by shorting the stirring time to 1-2 h.

Reference： [1]Tetrahedron,2012,vol. 68,p. 2858 - 2863

47
C₃₂H₄₂N₄O₈S [ No CAS ]
[ 1664-40-0 ]
C₃₈H₄₇N₅O₈S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With triethylamine; In ethanol; at 20℃; for 18h;	General procedure: To a solution of [(1S,2R)-3-[[[3-[(dimethylamino)methylene]-2,3-dihydro-2-oxo-1H- indol-5-yl]sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-carbamic acid, (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ester 8 (32 mg, 0.050 mmol) in absolute ethanol (1 ml) was added neopentylamine (29 mul, 0.25 mmol). The resulting solution was stirred 22 h and then concentrated in vacuo. The residue was purified on a preparative TLC plate (20 x 20 cm, 500 mum) using 8:2 EtOAc/hexane as eluant to provide [1-benzyl-3-({3-[(2,2-dimethyl-propylamino)-methylene]-2-oxo- 2,3-dihydro- 1H-indole-5-sulfonyl}-isobutyl-amino)-2-hydroxy-propyl]-carbamic acid hexahydro- furo[2,3-b]furan-3-yl ester 9n (24 mg, 70%). MS m/z 685.3 (MH)+, 1H NMR (CDCl3) 9.15 (m, 1H), 8.70 (s, 1H), 7.66 (s, 1H), 7.61 (d, J = 13.2, 1H),7.43 (dd, J = 8.4, 2.0, 1H), 7.24 (m, 5H), 7.00 (d, J = 8.0, 1H), 5.64 (d, J = 5.2, 1H), 5.11 (d, J = 8.4, 1H), 5.00 (m, 1H), 3.65 - 3.93 (m, 7H), 3.18 (d, J = 6.8, 2H), 2.75 - 3.22 (m, 7H), 1.83 (m, 1H), 1.60 (m, 1H), 1.42 (m, 1H), 1.01 (s, 9H), 0.84 - 0.95 (m, 6H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5078 - 5083

48
[ 1664-40-0 ]
[ 123-31-9 ]
[ 1394286-77-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	In methanol; at 20℃; for 1h;	Hydroquinone (1.0 mmol, 0.11 g) and N-phenylethylene-1,2-diamine (1.0 mmol, 0.14 g) were mixed in methanol, and stirred at room temperature for 1 h. The solution was changed from colorless to red. The methanol was evaporated to obtain red crystalline product of 1, which was washed with methanol, and dried in air. Yield: 93%. Anal. Calcd for C22H24N4O2: C, 70.2; H, 6.4; N, 14.9. Found: C, 70.0; H, 6.4; N, 15.0%. 1H NMR (DMSO-d6): 3.22 (t, 4H), 3.30 (t, 4H), 3.33 (s, 2H), 5.31 (s, 2H), 6.56 (m, 6H), 7.08 (t, 4H). 13C NMR (DMSO-d6): 40.8, 92.1, 111.9, 115.9, 128.9, 148.2, 151.1, 177.3. IR data (KBr, cm-1): 3397 (w), 3276 (m, sh), 1639 (vw), 1602 (m), 1550 (s), 1497 (s), 1443 (s), 1369 (w), 1301 (m), 1257 (w), 1179 (w), 1130 (w), 1096 (w), 875 (w), 816 (w), 753 (m), 698 (w), 670 (w), 515 (vw), 463 (vw). Single crystals of 1 suitable for X-ray diffraction were obtained by recrystallization of the product in methanol.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4889 - 4894

49
copper(II) perchlorate [ No CAS ]
[ 1664-40-0 ]
[ 119-67-5 ]
[ 1492906-03-2 ]

Yield	Reaction Conditions	Operation in experiment
63%		2-Formylbenzoic acid (1.0 mmol, 0.150 g), NEt3 (1.0 mmol,0.101 g), and <strong>[1664-40-0]N-phenylethane-1,2-diamine</strong> (1.0 mmol, 0.136 g) were dissolved in methanol (20 mL) with stirring. The mixture was stirred for 30 min at room temperature. To the above mixture was added with stirring a methanol solution (10 mL) of copper perchlorate (1.0 mmol, 0.373 g). The final mixture was further stirred for 1 h, and filtered. Green block-shaped single crystals of the complex were formed by slow evaporation of the solution.Yield: 63% on the basis of 2-formylbenzoic acid. Anal. Calcd.for C32H32CuN4O5 (FW 616.2): C, 62.4; H, 5.2; N, 9.1. Found:C, 62.2; H, 5.4; N, 9.0%.

Reference： [1]Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry,2013,vol. 43,p. 1406 - 1410

50
[ 1664-40-0 ]
[ 108-90-7 ]
[ 150-61-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With LiHMDS at 20℃; for 2h;
91%	With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; sodium t-butanolate In toluene at 110℃; for 12h; Inert atmosphere; Glovebox; chemoselective reaction;

Reference： [1]Wheaton, Craig A.; Bow, John-Paul J.; Stradiotto, Mark [Organometallics, 2013, vol. 32, # 21, p. 6148 - 6161]
[2]Crawford, Sarah M.; Lavery, Christopher B.; Stradiotto, Mark [Chemistry - A European Journal, 2013, vol. 19, # 49, p. 16760 - 16771]

51
[ 3612-20-2 ]
[ 88333-03-3 ]
[ 59768-74-0 ]
[ 1664-40-0 ]
methyl (S)-4-((N-benzyl-4-(benzylcarbamoyl)piperidin-4-yl)(2-phenethyl)amino)-3-((tert-butoxycarbonyl)amino)-4-oxobutanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%		General procedure: To a solution of the ketone (1.32mmol) in methanol (2mL) were added successively 2equiv of the corresponding amine, 2equiv of the amino acid and 2equiv of the isocyanide. The resulting mixture was stirred at room temperature for 4 days. Then, a 1.2M solution of HCl in MeOH was added and the mixture was stirred at room temperature for 30min. The solvent was removed under reduced pressure. The residue was redissolved in ethyl acetate and was successively washed with saturated NaHCO3 (3× 10mL) and brine (3× 10mL). The organic phase was dried (MgSO4), filtered and evaporated to dryness. The final residue was purified by flash column chromatography (hexane:ethyl acetate, 4:1 to 0:1) to give the target products 1-38.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 83,p. 174 - 189

52
[ 1448676-37-6 ]
[ 1664-40-0 ]
[ 1616294-12-2 ]

Yield	Reaction Conditions	Operation in experiment
24%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 17h;	A mixture of N'-phenyl-ethane-l^-diamine (40 mg, 0.29 mmol), 4-chloro-2-cyclopropyl-6,7- dimethoxy-quinazoline (77 mg, 0.29 mmol) and K2CO3 (61 mg, 0.44 mmol) in DMF (3 mL) was stirred at 60 C for 17 h. The reaction mixture was cooled to room temperture, diluted with EtOAc (80 mL) and the suspension was stirred for another 10 minutes. The suspension was washed with water (30 mL), brine (30 mL x2), dried over anhydrous Na2S04 and filtered. The filtrate was evaporated in vacuum to residue, which was purified by prep-TLC (PE/EtOAc = 1/2, 0.5% TEA as additive) to give compound (97), (25 mg, yield: 24%) as white solid. [00394] NMR (300 HMz, DMSO-i/6): delta = 7.93 (brs, 1H), 7.51 (s, 1H), 7.09 (m, J= 7.5 Hz, 2H), 6.99 (s, 1H), 6.68 (d, J= 7.8 Hz, 2H), 6.53 (t, J= 7.2 Hz, 1H), 5.82 (brs, 1H), 3.87 (s, 3H), 3.85 (s, 3H), 3.71- 3.60 (m, 2H), 3.33-3.20 (m, 2H), 2.06-1.93 (m, 1H), 1.08-1.00 (m, 2H), 0.95-0.84 (m, 2H). MS: m/z 365.2 (M+H+).

Reference： [1]Patent: WO2014/100501,2014,A1 .Location in patent: Paragraph 00393; 00394

53
[ 1549775-51-0 ]
[ 1664-40-0 ]
[ 1549772-19-1 ]

Yield	Reaction Conditions	Operation in experiment
0.020 g	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90℃; for 16h;Sealed tube; Inert atmosphere;	General procedure: The title compound was prepared using the methods shown in Scheme 2 with the appropriate amine in step 2, amide coupling (3-pyridylamine) and the appropriate amine in step 3, Buchwald coupling (NR4R5) (2-aminopyridine) reagents. 6-bromo-2-(furan-2-yl)-N-(pyridin-3-yl)quinoline-4-carboxamide (prepared as described above, 0.080 g) was added to a sealed tube and dissolved in toluene (5 ml). The vessel was purged with argon for 5 minutes, and 2-aminopyridine (0.029 g, 1.50 eq.) was then added. The vessel was purged with argon for an additional 5 minutes, cesium carbonate (0.200 g) was added, and the tube was purged with argon for an additional 15 minutes. DavePhos (2-(2-dicyclohexylphosphanylphenyl)-N,N-dimethylaniline, 0.012 g) and Pd2(dba)3 (tris(dibenzylideneacetone)dipalladium(0), 0.014 g) were added, the tube was flushed with argon and sealed. The reaction mixture was heated to 90 C. for 16 hours, and completion of the reaction was monitored by TLC using ethyl acetate:hexanes (5:5) as a mobile phase. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (10 ml), filtered through celite bed, which was washed with ethyl acetate (3*10 ml). The ethyl acetate was removed by distillation and the crude product was subjected to silica gel column chromatography purification. Elution of the compound with 20% ethyl acetate in hexanes provided 2-(furan-2-yl)-6-(pyridin-2-ylamino)-N-(pyridin-3-yl)quinoline-4-carboxamide (0.015 g). The title compound was prepared using the methods shown in Scheme 4 with the appropriate amine in step 2, amide coupling (3-pyridylamine) and the appropriate amine in step 3, l3uchwald coupling (NR4R5) (Ni -phenylethane-1, 2-diamine) to provide the title compound (0.020 g). ?H NMR (400 MHz, DMSO-d5) oe ppm 10.96 (s, 1H), 8.96 (s, 1H), 8.39 (m, 1H), 8.32 (m, 1H), 8.25 (m, 1H), 7.98 (s, 1H), 7.90 (m, 1H), 7.82 (m, 1H), 7.46 (m, 1H), 7.33 (m, 1H), 7.26 (m, 1H),7.06 (m, 2H), 7.02 (m, 1H), 6.71 (m, 1H), 6.57 (m, 2H), 7.51 (m, 1H), 5.68 (broad s, 1H), 3.29 (m, 4H); mlz 450.3 (MH]+.

Reference： [1]Patent: US2014/221387,2014,A1 .Location in patent: Paragraph 0372; 0377

54
[ 931-53-3 ]
[ 1664-40-0 ]
1-cyclohexyl-3-[2-(phenylamino)ethyl]thiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With sulfur; at 20℃; for 2h;	General procedure: A 10-mL test tube equipped with a magnetic stir bar was chargedwith an isocyanide 1 (1 mmol, 1 equiv), elemental sulfur (38.4 mg,1.2 mmol, 1.2 equiv) and an amine 2 (1.2 mmol, 1.2 equiv). The resulting mixture was stirred for the indicated time at the indicated temperature (see Schemes 2 and 4). Toluene (0.1 mL) can be added if necessary to facilitate the stirring. The crude mixture (oily or solid)was purified by silica gel column chromatography (eluent: appropriatemixtures of heptane-EtOAc, heptane-CH2Cl2 or CH2Cl2-MeOH).

Reference： [1]Synthesis,2014,vol. 46,p. 3172 - 3179

55
[ 108-86-1 ]
[ 107-15-3 ]
[ 1664-40-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	With chitosan Cu2+ complex; In acetonitrile; for 5h;Reflux; Green chemistry;	General procedure: Aryl halide (1.0 equiv) and aliphatic diamines/amino alcohol (2.0 equiv) were taken in a 100 ml round bottom flask along with 100-150 mg of the chitosan copper catalyst in CH3CN (15 ml) solvent. The resultant mixture was heated at reflux for 3-6 h. After completion of the reaction (the complete consumption of starting materials was confirmed by TLC) the reaction mixture was extracted with ethylacetate. The separated organic phase was concentrated to get the gummy liquid product 3. The chitosan copper catalyst was collected by simple decanting off the reaction mixture. The recovered catalyst was then washed thoroughly with ethyl acetate 2-3 times,dried under vacuum at 50C and used for another run.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 419 - 424

56
[ 85264-33-1 ]
[ 1664-40-0 ]
N,N-bis(3,5-dimethyl-1H-pyrazol-1-yl)methyl-N2-phenylethane-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	In acetonitrile; at 20℃; for 72h;	A solution of N-(3,5-dimethyl-1H-pyrazole-1-yl)methanol (0.252 g, 2 mmol) in acetonitrile (20 ml) was added to a stirred solution of N-(2-aminoethyl)benzenamine (0.136 g, 1 mmol) in acetonitrile (20 ml) at room temperature and stirring was continued for three days. The resulting solution was then dried over anhydrous Na2SO4 and solvent was removed on a vacuum rotary evaporator. A light-yellow viscous liquid was obtained. Purity ofthe compound was checked by TLC. Yield. 0.290 g (82%). Found C = 67.97, H = 8.05, N = 23.98 %, Elemental analysis Calc. for C20H28N6: C = 68.15, H = 8.01, N = 23.84 %. IR (neat) cm-1; nu(-NH), 3200 m; nu(C=C), 1615 s; nu(C=C) + nu(C=N)/pz ring, 1553s, 1467 s; 1H NMR (400 MHz, CDCl3, 20 C), d/ppm: 2.240-2.326 (s, 12H,4 -CH3 of pz), 3.142-3.174 (t, J = 6.4 Hz, 2H, -NH-CH2-CH2 of ethylene),3.376-3.392 (t, J = 6.4 Hz, 2H, -NH-CH2-CH2 of ethylene), 4.2 (s, 2H, N-CH2-N), 4.921 (s, 2H, N-CH2-N), 5.843 (s, 1H, pz ring), 5.853 (s, 1H, pz ring), 6.517 (d, 2H, J = 7.6 Hz, phenyl ring), 6.723 (t,1H, J = 7.2 Hz, phenyl ring), 7.213-7.256 (m, 2H, phenyl ring). MS (EI): m/z 353 (100%) (C20H28N6)+.

Reference： [1]Polyhedron,2015,vol. 100,p. 206 - 214

57
[ 75-15-0 ]
[ 27996-87-8 ]
[ 1664-40-0 ]
(RS)-9-nitro-1-phenyl-1,2,3,10b-tetrahydro-5H-benzo[e]imidazo[1,2-c][1,3]thiazine-5-thione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	In N,N-dimethyl-formamide; at 0 - 20℃; for 15h;	General procedure: 2-Fluoro-5-nitrobenzaldehyde (1.0 mmol, 1.0 equiv) was dissolved in anhydrous DMF (2 mL). A solution of the respective amine (2.0 mmol, 2.0 equiv) in 2 mL anhydrous DMF and then CS2 (3.0 mmol, 1.0 equiv) were added at 0 C. After stirring 15 h at room temperature, ethyl acetate (40 mL) was added. The solution was washed with brine (80 mL) and the aqueous layer was extracted with ethyl acetate (340 mL). The combined organic layers were dried (MgSO4), and the solvent was removed (rotary evaporator). The crude mixture was purified by column chromatography on silica gel. 4.2.1.24 (RS)-9-Nitro-1-phenyl-1,2,3,10b-tetrahydro-5H-benzo[e]imidazo[1,2-c][1,3]thiazine-5-thione (4e) Following GP A, 2-fluoro-5-nitrobenzaldehyde (169 mg, 1.00 mmol), <strong>[1664-40-0]N-phenylethylenediamine</strong> (272 mg, 2.00 mmol) and CS2 (228 mg, 3.00 mmol) were used. Column chromatography on silica gel (CH2Cl2; Rf=0.83) provided the desired product 4e as a yellow solid (170 mg, 50%, mp: 226-228 C (CH2Cl2)). IR (ATR): ?=3080 (w), 3062 (w), 3040 (w), 2981 (w), 2949 (w), 2920 (w), 2893 (w), 2844 (w), 1598 (m), 1578 (m), 1515 (m), 1437 (m), 1334 (s), 1240 (m), 1171 (m), 998 (m), 930 (m), 756 (s), 739 (s) cm-1; 1H NMR (500.1 MHz, DMSO-d6): delta=8.30 (dd, 3JH,H=8.6 Hz, 4JH,H=2.3 Hz, 1H, p-CHArCH), 7.85 (d, 3JH,H=8.6 Hz, 1H, m-CHArCH), 7.77 (d, 4JH,H=2.0 Hz, 1H, o-CHArCH), 7.30-7.27 (m, 2H, m-CHArN), 6.90-6.87 (m, 1H, p-CHArN), 6.84-6.82 (m, 2H, o-CHArN), 6.05 (s, 1H, NCH), 4.15-3.95 (m, 4H, CH2) ppm; 13C NMR (125.8 MHz, DMSO-d6): delta=181.9 (CS), 146.8 (CArNO2), 145.9 (CArN), 139.6 (CArS), 132.7 (CArCH), 129.4 (2m-CHArN), 126.6 (m-CHArCH), 124.0 (p-CHArCH), 119.4, 119.1 (o-CHArCH, p-CHArN), 113.8 (2o-CHArN), 76.3 (NCH), 49.6, 46.7 (CH2) ppm; MS (EI, 70 eV): m/z (%)=343.1 (100) [M]+; HRMS (EI, 70 eV): m/z calcd for [C16H13N3O2S2]+: 343.0444, found: 343.0436.

Reference： [1]Tetrahedron,2015,vol. 71,p. 8290 - 8301

58
[ 41167-58-2 ]
[ 1664-40-0 ]
(Z)-3-(2-oxo-2-phenylethylidene)-1-phenyl-piperazin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With acetic acid; In toluene; for 1h;Reflux;	To 15.0 g (72.7 mmol) of methyl 4-aryl-2-hydroxy-4-oxobut-2-enoate in a mixture of 100 mL of toluene and 40 mL of glacial acetic acid was added 9.5 mL (72.7 mmol) of <strong>[1664-40-0]N-phenylethylenediamine</strong>, and the reaction mixture was boiled for 1 h (TLC monitoring), evaporated to 40 mL volume, the precipitate was filtered off. Yield 92%, mp 154-156C (toluene). IR spectrum, nu, cm-1: 3214 br (NH in intramolecular hydrogen bond), 1671 (C2=O), 1607 br (COPh). 1H NMR spectrum (DMSO-d6), delta, ppm: 3.70 m (2H, C5H2), 3.97 m (2H, C6H2), 6.60 s (1H, C3=CH), 7.31 m (1Harom), 7.42-7.56 group of signals (7Harom), 7.89 d (2H, Ho in COPh, J 6.8 Hz), 10.86 s (1H, NH). Found, %: C 73.83; H 5.38; N 9.65. C18H16N2O2. Calculated, %: C 73.95; H 5.52; N 9.58. Compounds 1b and 1c were synthesized similarly.

Reference： [1]Russian Journal of Organic Chemistry,2015,vol. 51,p. 1587 - 1592
Zh. Org. Khim.,2015,vol. 51,p. 1617 - 1622,6

59
[ 41167-59-3 ]
[ 1664-40-0 ]
(Z)-3-[2-oxo-2-(4-chlorophenyl)ethylidene]-1-phenylpiperazin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With acetic acid; In toluene; for 1h;Reflux;	General procedure: To 15.0 g (72.7 mmol) of methyl 4-aryl-2-hydroxy-4-oxobut-2-enoate in a mixture of 100 mL of toluene and 40 mL of glacial acetic acid was added 9.5 mL (72.7 mmol) of <strong>[1664-40-0]N-phenylethylenediamine</strong>, and the reaction mixture was boiled for 1 h (TLC monitoring), evaporated to 40 mL volume, the precipitate was filtered off.

Reference： [1]Russian Journal of Organic Chemistry,2015,vol. 51,p. 1587 - 1592
Zh. Org. Khim.,2015,vol. 51,p. 1617 - 1622,6

60
[ 59001-10-4 ]
[ 1664-40-0 ]
C₁₇H₂₃N₃ [ No CAS ]

Reference： [1]Dalton Transactions,2015,vol. 44,p. 16073 - 16080

61
N-(4-chlorophenyl)-N-pentanoyl-4-nitrobenzenesulfonamide [ No CAS ]
[ 1664-40-0 ]
N-(2-(phenylamino)ethyl)pentanamide [ No CAS ]
[ 16937-03-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate; In water; at 80℃; for 0.166667h;Green chemistry;	General procedure: A mixture of the acylating reagents 1a-e (0.5 mmol),diamines or amino alcohol (0.5 mmol), and K2CO3 (1 mmolfor diamines and 3 mmol for amino alcohol or aminophenol) was stirred in H2O (1-2 mL) at 80 C for the appropriateperiod of time. The progress of the reaction wasmonitored by TLC. Upon completion of the reaction, thesolvent of the mixture was evaporated. Then, acetone(10 mL) was added and K2CO3 was filtered off and washedwith additional solvent (20 mL). After evaporation of thesolvent, the crude product was purified by column chromatographyon silica gel to afford the pure products (compounds4a-f and 5a-g).

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2016,vol. 71,p. 95 - 104

62
N-benzoyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamide [ No CAS ]
[ 1664-40-0 ]
[ 13670-23-0 ]
[ 16937-03-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate; In water; at 80℃; for 0.666667h;Green chemistry;	General procedure: A mixture of the acylating reagents 1a-e (0.5 mmol),diamines or amino alcohol (0.5 mmol), and K2CO3 (1 mmolfor diamines and 3 mmol for amino alcohol or aminophenol) was stirred in H2O (1-2 mL) at 80 C for the appropriateperiod of time. The progress of the reaction wasmonitored by TLC. Upon completion of the reaction, thesolvent of the mixture was evaporated. Then, acetone(10 mL) was added and K2CO3 was filtered off and washedwith additional solvent (20 mL). After evaporation of thesolvent, the crude product was purified by column chromatographyon silica gel to afford the pure products (compounds4a-f and 5a-g).

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2016,vol. 71,p. 95 - 104

63
spirothiazamenthane [ No CAS ]
[ 1664-40-0 ]
N¹-phenyl-N²-(4,4,8-trimethyl-1-thia-3-azaspiro[4.5]dec-2-en-2-yl)ethane-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With toluene-4-sulfonic acid; In toluene; at 150℃; for 4h;Microwave irradiation;	General procedure: Spirothiazamenthane 3 (1.0 eq) was dissolved in toluene (0.1 M concentration) in a microwave vial and the solution was treated with amine (10 eq) and PTSA (20 mol %). This mixture was heated at 150 C using microwaves for 4 h. After cooling, the solvents were removed by evaporation and the resulting residue was taken up in 1:1 Et2O/2M NaOH. The layers were separated and the aqueous layer was extracted 2 × with Et2O. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The resulting crude products were purified as described below. Variations in reaction conditions are also noted below.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 120,p. 64 - 73

64
[ 66-72-8 ]
[ 1664-40-0 ]
(Z)-5-(hydroxymethyl)-2-methyl-4-[2-(phenylamino)ethylimino]methyl}pyridin-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	In ethanol; at 40 - 50℃; for 1h;	A mixtureof 1.15 g of pyridoxal, 0.94 g of <strong>[1664-40-0]N-phenylethylenediamine</strong>, and 10 mL of ethanol was heated for 1 h at 40-50 C. After the solvent removal, the residue was recrystallized from ethanol-diethyl ether mixture (1 : 1). Yield 0.93 g (48%), mp 95-96 C. IR spectrum, nu, cm-1: 1633 (=N). 1 NMR spectrum (DMSO-d6), delta, ppm (J, Hz): 2.38 s (3H, CH3), 3.38 d.d (2, CH2, J = 11.5, 5.7), 3.86 t (2, CH2, J = 5.8), 4.64 s (2H, CH2OH), 5.41 s (1H, NH), 5.77 t (1H, CH2OH, J = 5.6), 6.54 t (1H, Ph, J = 7.2), 6.63 d (2H, Ph, J = 8.0), 7.08 t (2H, Ph, J = 7.6), 7.89 s (1H, CHAr), 8.90 s (1H, CH=). Mass spectrum (MALDI-TOF), m/z: 285.6 [M]+ .Found, %: C 66.92; H 7.51; N 14.70. C16H19N3O2. Calculated, %: C 67.37; H 6.67; N 14.74.

Reference： [1]Russian Journal of General Chemistry,2016,vol. 86,p. 607 - 612
Zh. Obshch. Khim.,2016,vol. 86,p. 466 - 471,6

65
[ 18507-89-6 ]
[ 1664-40-0 ]
C₃₀H₄₁N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In chloroform; for 24h;Reflux;	General procedure: (a) To a 100 mL two neck flask containing decoquinate 1 (1 g, 2.34 mmol) and DBU (320 muL, 0.33 g, 2.1 mmol, 0.9 eq.) in chloroform (25 mL) was added the primary or secondary amine (5 eq.). The resulting mixture was stirred under reflux for 24-72 h. Progress of the reactions was monitored by tlc. Upon completion, the reaction mixture was concentrated in vacuo. The concentrated residue was taken into chloroform (20 mL) and washed with distilled water (4 x 20 mL). The organic layer was dried (Na2SO4), filtered and the filtrate was evaporated to dryness to leave the crude product, which was subjected to flash column chromatography on silica gel. The product was eluted with a mixture of dichloromethane/methanol (10:1, v/v). The product was recrystallized from ethyl acetate and air dried. The amide derivatives 2-21 were thereby obtained in good yields using this procedure. Data for derivatives 2, 3 and 6 are given below.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3006 - 3009

66
[ 353507-85-4 ]
[ 1664-40-0 ]
4-[(2-anilinoethyl)amino]-6-chloro-5-nitro-2,1,3-benzoxadiazole-1-oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	In chloroform; at 20℃; for 1h;	N-Phenylethane-1,2-diamine, 0.05 mL (0.4 mmol), was added dropwise at room temperature to a solution of 0.1 g (0.4 mmol) of furoxan 1 in 5 mL of chloroform, and the mixture was stirred for 1 h at room temperature (TLC). The mixture was poured into 5 mL of hexane, and the precipitate was filtered off and dried under reduced pressure (0.06 mm) at 40C. Yield 71%, red-brown powder, mp 158C. IR spectrum (mineral oil), nu, cm-1: 3436, 3349 (NH); 1625 (furoxan), 1531 (NO2). 1H NMR spectrum, delta, ppm: 3.90 m (2H, CH2), 4.33 m (2H,CH2), 5.25 br.s (1H, NH), 6.61 t (1H, Harom, 3JHH =7.29 Hz), 6.71 m (2H, Harom), 6.81 s (1H, 7-H), 7.12 m (2H, Harom), 8.42 br.s (1H, NH). Found, %: C 48.15; H 3.51; Cl 10.02; N 20.18. C14H12ClN5O4. Calculated,%: C 48.08; H 3.46; Cl 10.14; N 20.03.

Reference： [1]Russian Journal of Organic Chemistry,2016,vol. 52,p. 920 - 921
Zh. Org. Khim.,2016,vol. 52,p. 924 - 925,2

67
4-(7-hydroxy-4-oxo-4H-benzopyran-3-yl)benzoic acid [ No CAS ]
[ 1664-40-0 ]
4-(7-hydroxy-4-oxo-4H-benzopyran-3-yl)-N-[2-(phenylamino)ethyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43.36%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; at 25℃; for 10h;	The 4 - (7-hydroxy 4-oxo -4H-benzopyran-3-alkenyl) benzoic acid (0.2g, 0 . 71mmol), EDCI (0.2g, 1 . 04mmol) and HOBT (0.1g, 0 . 74mmol) is placed in the reaction bottle, by adding 3mlDMF stirring to dissolve the solid mixture. In another reaction flask by adding N1-phenyl ethylenediamin (0.11g, 0 . 78mmol), then adding 2 ml anhydrous dichloromethane dissolved, the solution is poured into the raw material solution, 25 C stirring for 10 hours. After the reaction the reaction solution is poured into the 15 ml water, extracted with methylene chloride (50 ml × 3), merged methylene chloride level, saturated salt water for washing (50 ml × 3), dried anhydrous sodium sulfate, turns on lathe does. Column chromatography (dichloromethane: methanol =20 [...] 1, V/V), shall be 123 mg white solid, yield 43.36%.

Reference： [1]Patent: CN105541777,2016,A .Location in patent: Paragraph 0016; 0104; 0105; 0106

68
4-(7-acetoxy-4-oxo-4H-chromen-3-yl)benzoyl chloride [ No CAS ]
[ 1664-40-0 ]
4-(7-acetoxy-4 oxo-4H-benzopyran-3-yl)-N-[2-(phenylamino)ethyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63.44%	With triethylamine; In tetrahydrofuran; at 50℃; for 2h;	The N1-phenyl ethylenediamin (84 mg, 0 . 62mmol) is placed in the reaction bottle, by adding 5 ml of tetrahydrofuran is dissolved, add 4 - (7-acetoxy -4 oxo -4H-chromen-3-yl) benzoyl chloride (0.2g, 0 . 62mmol) and 0.2 ml triethylamine, 50 C reaction 2 hours. After the reaction is complete, the reaction solution is poured into 30 ml water, extracted with methylene chloride (50 ml × 3), merged methylene chloride level, saturated salt water for washing (50 ml × 3), dried anhydrous sodium sulfate, turns on lathe does. Column chromatography (dichloromethane: methanol =20 [...] 1, V/V), shall be 173 mg white solid, yield 63.44%.

Reference： [1]Patent: CN105541777,2016,A .Location in patent: Paragraph 0016; 0128; 0129; 0130

69
[ 34619-03-9 ]
[ 1664-40-0 ]
N-t-Butoxycarbonyl-N'-phenylethylenediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In methanol; for 4h;	<strong>[1664-40-0]N-phenylethylenediamine</strong> (2)(1.0 mmol) and di-tert-butyl carbonate(1.2 mmol) was dissolved in 15 ml of methanol,The reaction was stirred for 4 hours, Concentration under reduced pressure gave a brown oil. Column chromatography gave pure white solid compound (3),Yield 92%.

Reference： [1]Patent: CN103948587,2016,B .Location in patent: Paragraph 0031; 0038; 0039

70
[ 1664-40-0 ]
tetramethylammonium trifluoromethanethiolate [ No CAS ]
[ 16099-65-3 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 1831 - 1833

71
5-(4-bromo-N-(4-bromobenzyl)phenylsulfonamido)-3-methylbenzofuran-2-carboxylic acid [ No CAS ]
[ 1664-40-0 ]
5-(4-bromo-N-(4-bromobenzyl)phenylsulfonamido)-3-methyl-N-(2-(phenylamino)ethyl)benzofuran-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32.4%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 12h;	General procedure: To a stirring solution of compound 8 (200mg, 0.35mmol) in DCM (10mL) was added EDCI (91mg, 0.47mmol), HOBt (64mg, 0.47mmol) and the corresponding diamine derivatives (0.35mmol) with a drop of DIPEA. The reaction mixture was stirred for 12hat room temperature, then washed with diluted HCl and saturated brines. The organic layer were combined and dried over anhydrous Na2SO4, concentrated in vacuo, and then purified by flash chromatography to give product 9b-9h, 9k-9x, respectively.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 137,p. 45 - 62

72
[ 1664-40-0 ]
2,6-dimethylimidazo[1,2-a]pyrimidine-3-carboxylic acid [ No CAS ]
2,6-dimethyl-N-(2-(phenylamino)ethyl)imidazo[1,2-a]pyridine-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In dichloromethane; at 20℃;	General procedure: To a stirred solution of compounds 21a, b (0.5mmol) in anhydrous DCM (20mL) was added BOP-Cl (0.6mmol), Et3N (1.5mmol) and the amino parts (3, 4, 8a-l, 9a-d, 13a,b, 14a,b, 16a-i, 18, 22a,b and 23) at room temperature. The mixture was stirred overnight at the same temperature, and washed by H3PO4 solution (1%), saturated NaHCO3 solution and brine, dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by Flash column chromatography (DCM/MeOH, 0-10%) to afford the crude target compounds as yellow solids. The solid was further purified by treating with EtOAc and hexane (11mL, 1: 10) to yield the target compounds (24, 25, 26a-l, 27a-g, 28a,b, 29a,b, 30a-i, 31, 32a,b, 33).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 137,p. 117 - 125

73
[ 15771-06-9 ]
[ 1664-40-0 ]
1-(2-anilinoethyl)-5-benzyloxy-2-(hydroxymethyl)pyridin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	In water; at 150℃; for 1.5h;Microwave irradiation;	A suspension of 5-benzyloxy-2-(hydroxymethyl)pyran-4-one (100 mg, 0.43 mmol) and N'- phenylethane-l,2-diamine (84.5muIota_, 0.65 mmol) in water (2 mL) was heated under microwave conditions at 150 C for 90 min. The solvent was removed in vacuo and the residue treated with 10% Na2C03 and CHCI3 and passed through a phase separator tube. After removing the organic solvent in vacuo, the residue was purified by automated normal-phase chromatography (0-20 % MeOH/DCM, 4 g silica gel cartridge). The product-containing fractions were combined and the solvent removed in vacuo to give l-(2-anilinoethyl)-5-benzyloxy-2-(hydroxymethyl)pyridin-4- one (58 mg, 38% yield) as a tan solid. MS, ES+, 351 (M+H)+,. XH NMR (400 MHz, DMSO-d6) delta 7.49 (s, 1 H), 7.31 - 7.40 (m, 5 H), 7.08 (t, 2 H, J=7.7 Hz), 6.52 - 6.60 (m, 3 H), 6.20 (s, 1 H), 5.80 (t, 1 H, J=6.1 Hz), 5.62 (t, 1 H, J=5.7 Hz), 4.92 (s, 2 H), 4.36 (d, 2 H, J=5.8 Hz), 4.03 (t, 2 H, J=6.2 Hz), 3.38 (m, 2 H).

Reference： [1]Patent: WO2017/91818,2017,A1 .Location in patent: Page/Page column 145-146

74
2-chloro-N-(2-methoxy-5-(methyl(2-methylquinolin-4-yl)amino)phenyl)acetamide [ No CAS ]
[ 1664-40-0 ]
N-(2-methoxy-5-(methyl(2-methylquinolin-4-yl)amino)phenyl)-2-((2-(phenylamino)ethyl)amino)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium carbonate; In acetonitrile; at 80℃; for 2h;	General procedure: To a solution of compound 14f (90 mg, 0.27 mmol, 1.0 equiv) inacetonitrile heated at 80 C was added 3-methylaminopropionitrile(0.32 mmol, 1.2 equiv) and potassium carbonate (0.54 mmol, 2.0equiv) refluxed for 2 h. The reaction mixture was cooled and thesolvent removed under reduced pressure. The residue was partitionedbetween brine and ethyl acetate. The aqueous layer wasextracted with ethyl acetate. The combined organics were driedover Na2SO4 and concentrated. The residue was purified by flashchromatography using dichloromethane and methanol (v/v, 9:1) aseluent to give the product 15a. Under the same conditions, 15b-ecan be obtained by replacing 3-methylaminopropionitrile with different amines.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 138,p. 1114 - 1125

75
[ 7305-09-1 ]
[ 1664-40-0 ]
N1-(3-methoxyphenyl)-N2-phenyl-1,2-ethanediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With (CyPFCy)Ni(o-tol)Cl; sodium t-butanolate; In 1,4-dioxane; at 25℃; for 16h;Inert atmosphere; Sealed tube;	General procedure: In a nitrogen-filled glovebox, pre-catalyst C1 (5-7.5 mol%), (hetero)aryl pseudohalide (1.0 equiv), base (2.2 equiv), and NH3 (0.5M solution in 1,4-dioxane, 0.96 mL, 0.48 mmol, 4 equiv) wereadded to a screw-capped vial containing a magnetic stir bar. Thevial was sealed with a cap containing a PTFE septum, removedfrom the glovebox, and placed in a temperature-controlled aluminumheating block set to 80 C, at which point magnetic stirringwas initiated. After 16 h, the vial was then removed fromthe heating block and was allowed to cool to ambient temperature.The crude product was purified by flash-column chromatographyto afford the purified product.

Reference： [1]Synlett,2017,vol. 28,p. 1652 - 1656

76
[ 82-44-0 ]
[ 1664-40-0 ]
C₂₂H₁₈N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With copper; potassium hydroxide; In N,N-dimethyl-formamide; at 100℃; for 10h;Inert atmosphere;	(1) in 100 ml of three-mouth flask is sequentially added in the 0.002 muM 1 - chloro anthraquinone, 0.002 muM N - (2 - amino-ethyl) aniline, 0.002 muM potassium hydroxide and 0.2 mmol copper powder, in the three-port flask into the nitrogen, then dropwise 5 ml N, N - dimethyl formamide, in the 100 C lower reaction 10 h. (2) after the reaction cooling step (1) of the obtained reaction solution, then the dichloromethane as the extractant, concentrated, vacuum drying, to obtain the red brown solid powder. The solid powder column chromatography purification, eluting agent is a mixture of methylene chloride and petroleum ether (the volume ratio of 1:2), to make the dye precursor Ia Of purified, separating the yield is 50%;

Reference： [1]Patent: CN107057401,2017,A .Location in patent: Page/Page column 6; 8; 9

77
[ 2631-77-8 ]
[ 1664-40-0 ]
2,4-diiodo-6-((2-phenylaminoethylimino)methyl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In methanol; at 20℃; for 0.5h;	The ligand (L) was synthesized by the condensation reaction inthe methanol (15 mL) solvent by stirring an equimolar mixture of3,5-diidosalicylaldehyde (0.136 g, 1 mmol) and <strong>[1664-40-0]N-phenylethylenediamine</strong>(0.374 g, 1 mmol) within 30 min at room temperature.The obtained yellow precipitate was filtered off undervacuum then washed thoroughly with cold methanol and dried invacuo over anhydrous CaCl2 (yield: 90%). The purity of ligand waschecked by TLC. The synthetic route of Schiff base ligand is shownin Scheme 1.

Reference： [1]Journal of Molecular Structure,2017,vol. 1149,p. 727 - 735

78
[ 587-04-2 ]
[ 1664-40-0 ]
N1-(3-chlorobenzyl)-N2-phenylethane-1,2-diamine dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		N 1 -phenylethane-1,2-diamine (0.50 g, 3.7 mmol) obtained in Synthesis Example 1-1,Acetic acid (catalytic amount) was added to a solution of 3-chlorobenzaldehyde (457.4 muL, 4.0 mmol) in methanol (10 mL).The reaction mixture was stirred at room temperature overnight.Sodium borohydride (139 mg, 3.7 mmol) was slowly added to the mixture,And the mixture was stirred at room temperature for 7 hours.The volatiles were evaporated in vacuo.A saturated aqueous solution of NaHCO 3 (10 mL) was added to the residue, and the mixture was extracted with CH 2 Cl 2 (10 mL × 2).The combined organic layers were washed with brine (10 mL × 1), dried over Na 2 SO 4, filtered and concentrated in vacuo.The obtained residue was purified by MPLC (CH 2 Cl 2: methanol = 99: 1 to 93: 7) to obtain the target compound as a yellow oil (798.6 mg).The resulting oil was dissolved in ethanol and an excess of 0.5 M hydrochloric acid in ethanol solution (HCl-EtOH) was added to the solution.Ethanol was evaporated in vacuo.The obtained residue was to washed with ethyl acetate obtain dihydrochloride (949.7 mg, 78%).

Reference： [1]Patent: JP2017/178811,2017,A .Location in patent: Paragraph 0291-0296

79
[ 100-52-7 ]
[ 1664-40-0 ]
[ 58077-34-2 ]

Yield	Reaction Conditions	Operation in experiment
		N 1 -phenylethane-1,2-diamine (670 mg, 4.9 mmol) obtained in Synthesis Example 1-1,To a methanol (10 mL) solution of benzaldehyde (552 muL, 5.4 mmol)Acetic acid (3 drops) was added.After stirring at room temperature for 1 hour,To the mixture at 0 C. was added sodium borohydride (186 mg, 4.9 mmol)Was slowly added.The reaction mixture was stirred at room temperature for 1 hour.The volatiles were evaporated in vacuo.A saturated aqueous solution of NaHCO 3 (10 mL) was added to the residue, and the mixture was extracted with CH 2 Cl 2 (10 mL × 2).The combined organic layers were washed with brine (20 mL × 1), dried over Na 2 SO 4, filtered and concentrated in vacuo.The obtained residue was purified by MPLC (CH 2 Cl 2: methanol = 99: 1 to 93: 7) to obtain the objective compound (N 1 -benzyl-N 2 -phenylethane-1,2-diamine) as a brown oil.

Reference： [1]Patent: JP2017/178811,2017,A .Location in patent: Paragraph 0185-0187; 0191-0193

80
[ 100-52-7 ]
[ 1664-40-0 ]
N1-benzyl-N2-phenylethane-1,2-diamine dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		To a solution of 1,2-diamine 6a (670 mg, 4.9 mmol), benzaldehyde(7a: 552 mL, 5.4 mmol) in MeOH (10 mL) was addedAcOH (3 drops). After being stirred for 1 h at room temperature,sodium borohydride (186 mg, 4.9 mmol) was slowly added to themixture at 0 C. The reaction mixture was stirred for 1 h at roomtemperature. The volatiles were evaporated in vacuo. SaturatedNaHCO3 aq. (10 mL) was added to the residue and extracted withCH2Cl2 (10 mL 2). The combined organic layers were washedwith brine (20 mL 1), dried over Na2SO4, filtered off and concentratedin vacuo. The resultant residue was purified by MPLC (CH2-Cl2/MeOH = 99:1 to 93:7) to give a brown oil. 1H NMR (400 MHz,CDCl3) d 7.38-7.28 (m, 5H), 7.15 (t, J = 8.4 Hz, 2H), 6.69 (t, J = 7.6Hz, 1H), 6.62 (d, J = 8.8 Hz, 2H), 3.87 (s, 2H), 3.33 (t, J = 6.0 Hz,2H), 2.95 (t, J = 6.0 Hz, 2H); 13C NMR (150 MHz, CDCl3) d 147.7,135.9, 129.3, 128.9, 128.8, 128.1, 117.6, 112.9, 52.4, 46.7, 41.9.The obtained oil was dissolved in EtOH and excess amount of0.5 M HCl-EtOH was added to the solution. EtOH was evaporatedin vacuo. The resultant residue was washed with AcOEt to givedihydrochloride 8a (1.08 g, 73% yield).

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 775 - 785

81
[ 19163-21-4 ]
[ 1664-40-0 ]
C₁₉H₁₈N₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With acetic acid In ethanol at 65℃; for 72h;

Reference： [1]Ferreira, Jorge; Zilz, Raquel; Boeira, Igor S.; da Silva, Sabrina M.; Casagrande, Adriana C.A.; Casagrande, Osvaldo L. [Applied Organometallic Chemistry, 2019, vol. 33, # 3]

82
[ 1664-40-0 ]
[ 93-91-4 ]
1-phenyl-3-((2-(phenylamino)ethyl)amino)but-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With toluene-4-sulfonic acid; In methanol; at 60℃; for 24h;	Benzoylacetone (2.00 g, 12.50 mmol, 1.0 equiv) and p-toluenesulfonicacid (0.06 g, 0.35 mmol, 0.03 equiv) in 20 mL of methanolwere added to a solution of N-phenylethylendiamine (2.00 mL,15.00 mmol, 1.2 equiv) in 10 mL of methanol. The reaction mixturewas stirred at 60 C for 24 h. After cooling to room temperature,colorless crystals were obtained. The mother liquors were concentratedand stored at 4 C to allow the crystallization affording morecrystals. Filtration and subsequent evaporation of the solventsyielded the pure ligand H-L1 (3.30 g, 11.80 mmol, 94%) as colorlesscrystals. m.p.: 120-122 C. FT-IR (mmax/cm1, KBr): 3340 m(N-H),1607 m(CN). Elemental Anal. Calc. C18H20N2O: C, 77.11; H, 7.19;N, 9.99. Found: C, 76.83; H, 7.46; N, 10.14%. 1H NMR (500 MHz,CDCl3, 25C)delta = 2.02 (s, 3H, MeCN), 3.44 (d, 3JH-H = 3.7 Hz, 2H,CH2NH), 3.55 (m, 2H, CH2CN), 4.01 (br. s, 1H, NH), 5.70 (s, 1H,CH), 6.65, 6.74, 7.20, 7.42, 7.86 (d, t, t, m, d, 2:1:2:3:2, 10H, all aromaticsCH), 11.54 (s, 1H, NH O). 13C{1H} NMR (126 MHz, CDCl3,25 C): delta = 19.62 (MeCN), 42.47 (CH2CN), 44.00 (CH2NH), 92.75(CH), 113.05, 118.06, 126.99, 128.30, 129.52, 130.67 (all aromaticsCH), 140.36, 147.30 (Cq), 165.18 (CN), 188.14 (CO).

Reference： [1]Polyhedron,2019,vol. 162,p. 207 - 218

83
[ 100865-05-2 ]
[ 1664-40-0 ]
C₂₃H₂₃N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In 2-methoxy-ethanol; for 3h;Reflux;	N-Phenylethylenediamine 0.3 mL (2.10 mmol) was added to a solution of compound Rb 100 mg (0.266 mmol) in 2-methoxyethanol (3 mL), and then the resulting reaction mixture was reflux for 3h. After that the solution temperature was bring in to room temperature to afford yellow needle crystals. The obtained product was collected by filtration and washed with ethanol, then dried in a vacuum oven for overnight at room temperature to give desired product. yellow crystal in 87% yield (120 mg). Mp: 203.5-204.1 C. 1H-NMR (CDCl3, 400 MHz) delta 0.94 (t, J = 7.2 Hz, 3H), 1.27 (m, J = 7.2 Hz, 2H), 1.77 (m, J = 7.2 Hz, 2H), 3.65 (s, 4H), 3.96 (s, 1H), 4.11 (t, J = 7.2 Hz, 1H), 6.70 (t, J = 7.6 Hz, 3H) 6.81 (d, J = 7.2 Hz, 1H), 7.24 (t, J = 8.4 Hz, 2H), 7.58 (d, J = 7.2 Hz, 1H), 7.99 (t, J = 7.6 Hz, 1H), 8.43 (d, J = 8.4 Hz, 1H), 8.55 (d, J = 8.4 Hz, 1H). 13C-NMR (CDCl3, 125 MHz) delta 14.06, 20.67, 30.61, 40.03, 43.47, 44.04, 107.25, 112.04, 112.75, 113.59, 119.01, 129.80, 132.26, 133.62, 147.89, 152.21, 164.66. IR (KBr, cm-1): 3328, 3058, 2961, 2934, 1673, 1626, 1603, 1513, 1499, 1310, 996 MS (HRMS): m/z calcd for C3H3O3N3: [M+H]+ 388.0967, found 388.1046, [M+Na]+ 410.0787, found 410.0887.1H/13C NMR and HRMS spectrum of R1 were shown in Fig. S1, S2 ,S3 and S4 respectively

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 3858 - 3862

84
[ 201230-82-2 ]
[ 1664-40-0 ]
[ 111154-10-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2019

85
1,5-bis(4-chlorophenyl)-2-methyl-1H-pyrrole-3-carbaldehyde [ No CAS ]
[ 1664-40-0 ]
N-((1,5-bis(4-chlorophenyl)-2-methyl-1H-pyrrol-3-yl)methyl)-N₂-phenylethane-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%		General procedure: The appropriate aldehyde 7a-n (1 mmol) was dissolved in 5mLof THF in a round-bottom flask. AcOH (1 mmol) and the appropriateamine (1.2 mmol) were added to the mixture and allowed to stir atroom temperature for 30 min before the addition of NaB(AcO)3H(3 mmol). The mixture was then allowed to stir at room temperaturefor 24 h. After completion, the reactionwas quenched with 1MNaOH solution (25 mL). The mixture was allowed to stir for afurther 30 min, before the mixture was diluted with EtOAc (10 mL)and washed twice with EtOAc (10 mL) and once with brine (20 mL).The organic extracts were collected, dried over MgSO4, filtered andconcentrated under reduced pressure. The crude residue was purifiedwith flash chromatography (EtOAc/MeOH 9:1 v/v), affordingthe desired compounds 8c-v.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 178,p. 500 - 514

86
[ 37949-03-4 ]
[ 1664-40-0 ]
N₁-phenyl-N₂-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-7-yl)ethane-1,2-diamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 9450 - 9470

87
[ 1198-30-7 ]
[ 1664-40-0 ]
N1-(isoquinolin-1-yl)-N1-phenylethane-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With 1,4-diaza-bicyclo[2.2.2]octane; 1,3-dicyano-5-fluoro-2,4,6-tris(diphenylamino)benzene In acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;

Reference： [1]Zhou, Chao; Lei, Tao; Wei, Xiang-Zhu; Ye, Chen; Liu, Zan; Chen, Bin; Tung, Chen-Ho; Wu, Li-Zhu [Journal of the American Chemical Society, 2020, vol. 142, # 39, p. 16805 - 16813]

88
[ 1001-75-8 ]
[ 1664-40-0 ]
4-methyl-N-(2-(phenylamino)ethyl)-4-pentenamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5h;

Reference： [1]Shi, Lijun; Wen, Mingshan; Li, Fuwei [Chinese Journal of Chemistry, 2021, vol. 39, # 2, p. 317 - 322]

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	1664-40-0	MDL No. :	MFCD00008162
Formula :	C₈H₁₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OCIDXARMXNJACB-UHFFFAOYSA-N
M.W :	136.19	Pubchem ID :	74270
Synonyms :

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	3
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	43.26
TPSA :	38.05 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.73 cm/s

[ CAS No. 1664-40-0 ] {[proInfo.proName]}

Quality Control of [ 1664-40-0 ]

Related Doc. of [ 1664-40-0 ]

Product Details of [ 1664-40-0 ]

Calculated chemistry of [ 1664-40-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1664-40-0 ]

Application In Synthesis of [ 1664-40-0 ]

[ 1664-40-0 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 1664-40-0 ]

Aryls

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Log Po/w (iLOGP) :	1.6
Log Po/w (XLOGP3) :	0.56
Log Po/w (WLOGP) :	0.87
Log Po/w (MLOGP) :	1.21
Log Po/w (SILICOS-IT) :	0.98
Consensus Log Po/w :	1.04

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-1.28
Solubility :	7.1 mg/ml ; 0.0521 mol/l
Class :	Very soluble
Log S (Ali) :	-0.93
Solubility :	16.0 mg/ml ; 0.117 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.87
Solubility :	0.185 mg/ml ; 0.00136 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	2735
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 1664-40-0 ] {[proInfo.proName]}

Quality Control of [ 1664-40-0 ]

Related Doc. of [ 1664-40-0 ]

Product Details of [ 1664-40-0 ]

Calculated chemistry of [ 1664-40-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1664-40-0 ]

Application In Synthesis of [ 1664-40-0 ]

[ 1664-40-0 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 1664-40-0 ]

Aryls

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1664-40-0 ]