[ CAS No. 10220-22-1 ]

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Product Details of [ 10220-22-1 ]

CAS No. :	10220-22-1	MDL No. :	MFCD00020819
Formula :	C₁₀H₁₂N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	192.21 g/mol	Pubchem ID :	352305
Synonyms :

Safety of [ 10220-22-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 10220-22-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 10220-22-1 ]
Downstream synthetic route of [ 10220-22-1 ]

[ 10220-22-1 ] Synthesis Path-Upstream 1~2

1
[ 10220-22-1 ]
[ 2632-65-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 9 h; Inert atmosphere; Schlenk technique	General procedure: The nitrophenyl analogue 7a–7e (7.5 mmol) was dissolved in ethanol (50 mL), and to this solution was added 10percent Pd/C (0.2 g). The reaction mixture was stirred at room temperature under an atmosphere of H₂ for 9 h. After completion of the reaction, the resulting mixture was filtered through Celite. The filtrate was concentrated under high vacuum to afford the desired aniline derivatives 8a–8e.
80%	With ammonium hydroxide; sodium dithionite In water for 0.25 h; Reflux	General procedure: To a solution of 1-(substituted) 4-nitrobenzene IVa,b,e,f(0.01 mol) in NH4OH (20 mL, 30percent), a solution of sodium dithionite(7 g, 0.04 mol) in water (30 mL) was quickly added, the reactionmixture was refluxed for 15 min. After cooling, the crude productwas filtered, washed and crystallized from methylene chloride toyield target compounds Va,b,e,f. 4-(Pyrrolidin-1-yl) aniline Vb Yield 80percent as yellow oil, (as reported) [66] .
55%	With sodium hydroxide In ethanol; acetic acid; ethyl acetate	2) 4-(Pyrrolidin-1-yl)-phenylamine (8). To a solution of 7 in ethanol (20 mL) was added 10 wt percent Pd on carbon (Degussa) (25 mg, 23 .box.mol). Glacial acetic acid (2-3 drops) was added to the reaction. The reaction was placed under a H₂ atmosphere and stirred for 16 hours, after which the reaction mixture was filtered through a pad of celite. The filtrate was evaporated, and the residue then dissolved in ethyl acetate (20 mL) and washed with 2N HCl (aq. 15 mL). The aqueous phase was isolated and then basified by the addition of 2N NaOH (aq. 20 mL). The aqueous layer was extracted with ethyl acetate (20 mL*2). The ethyl acetate extracts were dried over anhydrous magnesium sulfate, filtered, and evaporated to give crude 8 as a yellow oil (642 mg, 55percent for 2 steps).

Reference： [1] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 7, p. 1863 - 1873
[2] Bioorganic Chemistry, 2014, vol. 57, p. 65 - 82
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 11, p. 2131 - 2137
[4] Patent: US2005/49286, 2005, A1,
[5] Justus Liebigs Annalen der Chemie, 1955, vol. 596, p. 1,151
[6] Journal of the American Chemical Society, 1948, vol. 70, p. 2223,2228
[7] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, <1951> 166, 168, [8] Chem.Abstr., 1951, p. 10236
[9] European Journal of Organic Chemistry, 2009, # 14, p. 2243 - 2250
[10] Patent: WO2014/189466, 2014, A1, . Location in patent: Paragraph 000121-000122
[11] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3057 - 3061
[12] Organic Letters, 2017, vol. 19, # 24, p. 6486 - 6489

2
[ 696-59-3 ]
[ 100-01-6 ]
[ 4533-42-0 ]
[ 10220-22-1 ]

Reference： [1] Synthesis, 1999, # 1, p. 74 - 79
[2] Synthesis, 1999, # 1, p. 74 - 79

[ 10220-22-1 ] Synthesis Path-Downstream 1~9

1
[ 10220-22-1 ]
[ 2632-65-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; for 9h;Inert atmosphere; Schlenk technique;	General procedure: The nitrophenyl analogue 7a-7e (7.5 mmol) was dissolved in ethanol (50 mL), and to this solution was added 10% Pd/C (0.2 g). The reaction mixture was stirred at room temperature under an atmosphere of H2 for 9 h. After completion of the reaction, the resulting mixture was filtered through Celite. The filtrate was concentrated under high vacuum to afford the desired aniline derivatives 8a-8e.
80%	With ammonium hydroxide; sodium dithionite; In water; for 0.25h;Reflux;	General procedure: To a solution of 1-(substituted) 4-nitrobenzene IVa,b,e,f(0.01 mol) in NH4OH (20 mL, 30%), a solution of sodium dithionite(7 g, 0.04 mol) in water (30 mL) was quickly added, the reactionmixture was refluxed for 15 min. After cooling, the crude productwas filtered, washed and crystallized from methylene chloride toyield target compounds Va,b,e,f. 4-(Pyrrolidin-1-yl) aniline Vb Yield 80% as yellow oil, (as reported) [66] .
59.28%	With iron; ammonium chloride; In ethanol; water; at 90℃;	To a stirred solution of 580 1-(4-nitrophenyl)pyrrolidine (0.60 g, 3.121 mmol, 1.0 eq) in 6 EtOH (20 mL) was added Fe(0) (1.395 g, 24.971 mmol, 8.0 eq) and a solution of 67 NH4Cl (1.67 g, 31.210 mmol, 10.0 eq) at rt. The resulting mixture was heated at 90 C. for 60 min. The progress of reaction was monitored by LCMS. The reaction mixture was filtered through celite the residue was washed with EtOH (50 mL) the filtrate was concentrated and the residue was dissolved in 19 EtOAc (50 mL), washed with water (2×50 mL), dried over Na2SO4, and concentrated to afford 583 4-(pyrrolidin-1-yl)aniline (0.30 g, 59.28%) as brown viscous. (0608) LCMS: 163.3 [M+1]+

55%	With sodium hydroxide;Pd on carbon; In ethanol; acetic acid; ethyl acetate;	2) 4-(Pyrrolidin-1-yl)-phenylamine (8). To a solution of 7 in ethanol (20 mL) was added 10 wt % Pd on carbon (Degussa) (25 mg, 23 mol). Glacial acetic acid (2-3 drops) was added to the reaction. The reaction was placed under a H2 atmosphere and stirred for 16 hours, after which the reaction mixture was filtered through a pad of celite. The filtrate was evaporated, and the residue then dissolved in ethyl acetate (20 mL) and washed with 2N HCl (aq. 15 mL). The aqueous phase was isolated and then basified by the addition of 2N NaOH (aq. 20 mL). The aqueous layer was extracted with ethyl acetate (20 mL*2). The ethyl acetate extracts were dried over anhydrous magnesium sulfate, filtered, and evaporated to give crude 8 as a yellow oil (642 mg, 55% for 2 steps).
	With hydrogen; In ethyl acetate; at 50℃; under 7500.75 Torr;	l-(4-nitrophenyl)pyrrolidine was dissolved in ethyl acetate (0.05 M) and reduced with H-cube at 50C, 10 bar. Reduction was completed in 2 cycles. The solvent was evaporated off in vacuo, and the crude purified using column chromatography to afford the product. 1H NMR (400 MHz, DMSO-d6) 6 (ppm): 6.49 (d, J=8.4 Hz, 2H), 6.34 (d, J-8.4 Hz), 4.24 (s, 2H), 3.07 (m, 4H), 1.87 (m, 4H). LC-MS: m/z 163 (M+H).
	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃;	General procedure: A suspension of 1.01 g (5 mmol) 1-bromo-4-nitrobenzene, 1.5 g K2CO3, 0.59 mL (6 mmol) piperidine in 10 mL of DMF was heated to reflux overnight. Upon cooling, the reaction mixture was dilute with water, extracted with EA, and the organic layer was washed with water, followed by saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography (PE : EA = 50:1, 30:1) to afford 902 mg (87%) yellow solid. The solid was dissolved in methanol, 90 mg Pd-C (10%) was added and stirred under hydrogen overnight at room temperature and then filtered through Celite and concentratedin vacuo. The crude product was purified by flash chromatography (PEEA = 5:1) to afford 4l? 0.706 g 99%.
	With 5%-palladium/activated carbon; hydrogen; In ethanol; water; at 20℃;	General procedure: The substituted nitro compound 11 (1 equiv in a mixture of EtOH-H2O, 95:5, 20mL) was treated with 10% Pd-carbon (5% w/w). The reaction was subjected to hydrogenation under hydrogen gas at room temperature and the reaction was monitored by TLC. After completion of the reaction, the mixture was filtered through a Celite bed and concentrated in a vacuum to afford product 12.

Reference： [1]New Journal of Chemistry,2019,vol. 43,p. 1764 - 1769
[2]Bulletin of the Korean Chemical Society,2015,vol. 36,p. 1863 - 1873
[3]Bioorganic Chemistry,2014,vol. 57,p. 65 - 82
[4]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2131 - 2137
[5]Patent: US2019/106436,2019,A1 .Location in patent: Paragraph 0604; 0607-0608
[6]Patent: US2005/49286,2005,A1
[7]Justus Liebigs Annalen der Chemie,1955,vol. 596,p. 1,151
[8]Journal of the American Chemical Society,1948,vol. 70,p. 2223,2228
[9]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, <1951> 166, 168,
Chem.Abstr.,1951,p. 10236
[10]European Journal of Organic Chemistry,2009,p. 2243 - 2250
[11]Patent: WO2014/189466,2014,A1 .Location in patent: Paragraph 000121-000122
[12]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3057 - 3061
[13]Organic Letters,2017,vol. 19,p. 6486 - 6489
[14]European Journal of Medicinal Chemistry,2019,vol. 163,p. 690 - 709
[15]New Journal of Chemistry,2019,vol. 43,p. 10190 - 10202

2
[ 123-75-1 ]
[ 14150-94-8 ]
[ 67-64-1 ]
[ 10220-22-1 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1982,vol. 55,p. 2174 - 2180

3
[ 7335-06-0 ]
[ 100-00-5 ]
[ 10220-22-1 ]
N-ethyl-N-(4-chlorobutyl)-p-nitroaniline [ No CAS ]
N-<4-(N-ethyl-p-nitrophenylamino)butyl>-N-ethylpyrrolidinium chloride [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1995,vol. 68,p. 2941 - 2950

4
[ 767-10-2 ]
[ 100-00-5 ]
[ 10220-22-1 ]
N-butyl-N-(4-chlorobutyl)-p-nitroaniline [ No CAS ]
N-<4-(N-butyl-p-nitrophenylamino)butyl>-N-butylpyrrolidinium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 49% 2: 1.6% 3: 2.4%	In tetrahydrofuran at 80℃; for 48h;
1: 2.4% 2: 1.6% 3: 49%	In tetrahydrofuran at 80℃; for 48h;

Reference： [1]Ibata, Toshikazu; Shang, Mu-Hong; Demura, Tetsuo [Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 10, p. 2941 - 2950]
[2]Ibata, Toshikazu; Shang, Mu-Hong; Demura, Tetsuo [Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 10, p. 2941 - 2950]

5
[ 29897-82-3 ]
[ 100-00-5 ]
[ 10220-22-1 ]
2-benzyl-1-(p-nitrophenyl)pyrrolidine [ No CAS ]
N,N'-dibenzylpyrrolidinium chloride [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1995,vol. 68,p. 2941 - 2950

6
[ 55-98-1 ]
[ 100-01-6 ]
[ 10220-22-1 ]

Reference： [1]Chinese Chemical Letters,2011,vol. 22,p. 276 - 279

7
[ 10220-22-1 ]
[ 25309-64-2 ]
1-(4-ethylphenyl)pyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With copper(l) iodide; In N,N-dimethyl-formamide; at 100℃; for 24h;	The 177 mu L (1.0mmol) 4- ethyl monoiodo-benzene, 167 mu L (2.0mmol) tetrahydrofurfuroxy pyrrolizinone, 100 mg sodium base montmorillonite clay, 0.0390g (0.2mmol) cuprous iodide, 0.5317g (2.5mmol) adding potassium phosphate 5mLN, in N-dimethyl formamide, 100 C reaction 24 hours, other steps of the embodiment 1 the same, to obtain a liquid N-(4-ethyl-phenyl) pyrrolidine, its yield is 75%, of the soil sodium Kimon escapes centrifugal separation to obtain the percent recovery of copper in 65%.

Reference： [1]Patent: CN104016897,2016,B .Location in patent: Paragraph 0023

8
[ 13691-26-4 ]
[ 2393-23-9 ]
[ 10220-22-1 ]
N<SUP>1</SUP>-(4-methoxybenzyl)-N<SUP>4</SUP>-(4-nitrophenyl)butane-1,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 39% 2: 40 %Chromat.	Stage #1: 1-(4-nitrophenyl)pyrrolidin-2-one With Schwartz's reagent In tetrahydrofuran at 0℃; for 1h; Sealed tube; Inert atmosphere; Stage #2: 4-methoxy-benzylamine With sodium tris(acetoxy)borohydride In tetrahydrofuran at 23℃; for 18h; Sealed tube; Inert atmosphere;

Reference： [1]Prince, Robin J.; Gao, Fang; Pazienza, Jessica E.; Marx, Isaac E.; Schulz, Jurgen; Hopkins, Brian T. [Journal of Organic Chemistry, 2019, vol. 84, # 12, p. 7936 - 7949]

9
[ 10220-22-1 ]
[ 124-38-9 ]
[ 13691-26-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium chlorate In lithium hydroxide monohydrate; acetonitrile at 60℃; for 1.5h; Green chemistry;	General procedure for the oxidation of tertiary amines to corresponding amides: General procedure: A solution of (4-nitrophenyl) morpholine (1.04 g, 5 mmol) in CH3CN (10mL) was added into a 100mL three-port roundbottomflask, and it was stirred under CO2 atmosphere at 50°C. Then a solution of sodium chlorite (morethan 80%, 1.69 g, 15mmol) in 5 mL water was added in 20 min. TLC and HPLC showed that the reactionwas completed in 2.5 h. The reaction was quenched with aqueous saturated sodium sulfite. The mixture wasextracted by DCM (3×30 mL). The combined organic solution was dried over anhydrous sodium sulphate.Removal of all volatiles heft a residue, which was purified by flash chromatography on silica gel(hexane/EtOAc, from 5:1 to 3:1) to give 1.05g (95% yield) of 2a as a light-yellow solid.

Reference： [1]Liu, Chaoyang; Sun, Haozhou; Qin, Cheng; Yang, Tiannuo; Zhang, Wenxian; Zhou, Yuan; Li, Yani; Jia, Zheng Robert; Chu, Changhu [Synlett, 2022, vol. 33, # 10, p. 993 - 997]

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[ CAS No. 10220-22-1 ]

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Product Details of [ 10220-22-1 ]

Safety of [ 10220-22-1 ]

Application In Synthesis of [ 10220-22-1 ]

[ 10220-22-1 ] Synthesis Path-Upstream 1~2

[ 10220-22-1 ] Synthesis Path-Downstream 1~9

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry