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Quality Control of [ 93138-55-7 ]

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Product Details of [ 93138-55-7 ]

CAS No. :	93138-55-7	MDL No. :	MFCD04114502
Formula :	C₁₂H₁₈N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SEJNYLBEEMVJNN-UHFFFAOYSA-N
M.W :	190.28	Pubchem ID :	6484331
Synonyms :

Safety of [ 93138-55-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 93138-55-7 ]

* 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 [ 93138-55-7 ]
Downstream synthetic route of [ 93138-55-7 ]

[ 93138-55-7 ] Synthesis Path-Upstream 1~2

1
[ 93138-55-7 ]
[ 73279-04-6 ]

Yield	Reaction Conditions	Operation in experiment
94.3%	With sulfuric acid; sodium nitrite In water at 0 - 85℃;	Add 1750 g of water to the reaction flask, cool to 10-15 °C, and add 500 g with stirring.(About 5.000 mol) concentrated sulfuric acid, controlled temperature below 30°C. After dropping,After cooling to 15° C., 475 g (2.50 mol) of Compound 7 prepared in Example 2 was added, and the mixture was stirred and completely dissolved. After cooling to 0° C. or lower, an aqueous solution containing 181 g (2.63 mol) of sodium nitrite was added dropwise.The temperature is controlled below 5°C.After completion of the dropwise addition, the incubation temperature is below 5°C for 0.5 hr. After TLC confirms that all reactions of compound 7 have been completed,Spare (stock solution 1).To another reaction flask was added 1250 g of water, and 375 g (about 3.75 mol) of concentrated sulfuric acid was added dropwise.After the dropwise addition was completed, heating was performed at a temperature of 75°C to 80°C. The stock solution 1 was added dropwise via a dropping funnel.The control temperature is 80 °C ± 5 °C. After the addition, securityThe reaction was carried out at a temperature of 80° C. to 85° C. for 6 hours to 8 hours, and the reaction was monitored by TLC. Until the diazonium salt disappears.After confirming the completion of the reaction, the reaction system is cooled to about 30°C.Then, 500 g of methanol was added, and about 1350 g (about 19.8 mol) of ammonia water was added dropwise, and the temperature was controlled below 60° C., and the pH was adjusted to be 9 to 10 (solids were precipitated during the alkalizing with ammonia).After the adjustment is completed, the system is cooled to 10° C. or less, and the crystallization is maintained for 3 to 4 hours. Filter, 60-80 °C blast drying. Light brown compound 1 was obtained with a dry weight of 450 g (theoretical amount: 477.45 g); yield: 94.3percent

Reference： [1] Patent: CN107698538, 2018, A, . Location in patent: Paragraph 0057-0060

2
[ 93138-55-7 ]
[ 93793-83-0 ]

Reference： [1] Patent: CN107698538, 2018, A,

[ 93138-55-7 ] Synthesis Path-Downstream 1~9

1
[ 93138-55-7 ]
[ 618-89-3 ]
N-(3-Methoxycarbonylbenzyl)-3-(piperidinomethyl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium hydride; In tetrahydrofuran; DMF (N,N-dimethyl-formamide); at 50℃; for 3.5h;	1-(3-Aminobenzyl)piperidine (0.52 g) obtained by the known process (WO99/32100) was dissolved in tetrahydrofuran (4.0 mL) and N,N-dimethylformamide (1.0 mL), and methyl 3-(bromomethyl)benzoate (0.63 g) and a 60% dispersion (0.013 g) of sodium hydride in mineral oil were added thereto, followed by stirring at 50 C. for 3.5 hours. The mixture was allowed to stand for cooling to room temperature, and then a saturated aqueous sodium bicarbonate solution and water were added thereto, followed by extraction with chloroform. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel preparative thin layer chromatography (chloroform:methanol=5:1) to give Compound X (0.67 g, 72%) as a pale yellow oily substance. [0583] 1H NMR (270 MHz, CDCl3) δ8.03 (1H, m), 7.91 (1H, m), 7.56 (1H, m), 7.38 (1H, t), 7.08 (1H, t), 6.71 (1H, m), 6.65 (1H, brd), 6.51 (1H, brdd), 4.48 (1H, brs), 4.37 (2H, brs), 3.89 (3H, s), 3.49 (2H, brs), 2.45 (4H, m), 1.61 (4H, m), 1.43 (2H, m).

Reference： [1]Patent: US2003/225288,2003,A1 .Location in patent: Page 31

2
[ 93138-55-7 ]
[ 67808-64-4 ]
N-(5-methoxycarbonyl-2-thenyl)-3-(piperidinomethyl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium tris(acetoxy)borohydride; In tetrahydrofuran; acetic acid;	Compound AA (0.19 g, 75percent) was obtained as pale yellow crystals using 1-(3-aminobenzyl)piperidine (0.16 g) obtained by the known process (WO99/32100), <strong>[67808-64-4]methyl 5-formyl-2-thiophenecarboxylate</strong> (0.12 g) obtained by the known method (J. Heterocycl. Chem., 28: 17-28 (1991)), sodium triacetoxyborohydride (0.89 g), acetic acid (0.25 mL) and tetrahydrofuran (5.0 mL) as described in Reference Example 6. [0592] 1H NMR (270 MHz, CDCl3) delta7.63 (1H, d), 7.09 (1H, t), 6.96 (1H, brd), 6.72-6.63 (2H, m), 6.52 (1H, m), 4.49 (2H, brs), 4.37 (1H, brs), 3.82 (3H, s), 3.41 (2H, brs), 2.38 (4H, m), 1.57 (4H, m), 1.42 (2H, m).

Reference： [1]Patent: US2003/225288,2003,A1 .Location in patent: Page 32

3
[ 93138-55-7 ]
[ 21860-07-1 ]
N-(3-Methoxycarbonyl-a-methylbenzyl)-3-(piperidinomethyl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With borane pyridine; In pyridine; dichloromethane; acetic acid; at 20℃; for 19h;	1-(3-Aminobenzyl)piperidine (1.1 g) obtained by the known process (WO99/32100) and <strong>[21860-07-1]methyl 3-acetylbenzoate</strong> (1.0 g) obtained by the known method (J. Med. Chem., 13: 674-680 (1970)) were dissolved in dichloromethane (4.0 mL) and acetic acid (1.2 mL), and borane-pyridine complex (a 8 mol/L solution in pyridine; 0.71 mL) was added thereto, followed by stirring at room temperature for 19 hours. Water and a saturated aqueous sodium bicarbonate solution were added thereto to adjust the pH to about 9, followed by stirring at room temperature for 30 minutes and extraction with chloroform. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel preparative thin layer chromatography (chloroform:methanol=8:1) to give Compound Y (0.53 g, 27%) as a pale yellow oily substance. [0586] 1H NMR (270 MHz, CDCl3) delta8.05 (1H, m), 7.88 (1H, m), 7.56 (1H, m), 7.35 (1H, t), 7.00 (1H, t), 6.64-6.48 (2H, m), 6.37 (1H, m), 4.53 (1H, brq), 4.24 (1H, brs), 3.88 (3H, s), 3.40 (2H, brs), 2.34 (4H, m), 1.56 (4H, m), 1.50 (3H, d), 1.39 (2H, m).

Reference： [1]Patent: US2003/225288,2003,A1 .Location in patent: Page 31-32

4
[ 59507-46-9 ]
[ 93138-55-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogen; In methanol; at 45 - 50℃; under 2280.15 Torr;	All oils obtained in Example 1 (calculated as a theoretical amount of 880 g, 3.995 mol;Compound 6) is added to the hydrogenation kettle, then 7700 g of methanol is added, and 176 g of catalyst Raney Ni is added after stirring.The catalyst was rinsed again with 1100 g of methanol and added to the hydrogenation kettle. Nitrogen replacement 2 or 3 times,The hydrogen gas was replaced 2 to 3 times, and then hydrogen was added at a pressure of about 3 atm and a temperature of 45 to 50C until the reaction was completed.After confirming the complete conversion of compound 6 to compound 7, it was cooled to room temperature, the catalyst was filtered, and the filtrate was collected and concentrated.Methanol was added to give a solid, which was dried to give Compound 7 as an off-white solid 730 g (theoretical amount: 760.26 g); Yield: 96.0%
	palladium; In ethanol;	REFERENCE EXAMPLE 17 In ethanol (100 ml) was dissolved 1-(3-nitrobenzyl)-piperidine (32.2 g), and to the mixture was added dried 10% palladium on carbon (1.61 g). Under hydrogen atmosphere, the mixture was stirred at room temperature under atmospheric pressure for 24 hours. The palladium was filtered off, and the filtrate was concentrated. The residue was recrystallized from diisopropylether-hexane to give 1-(3-aminobenzyl)piperidine (15.8 g) as colorless crystals. mp 109-110 C.; Elemental Analysis for C12 H18 N2; Calcd: C, 75.74; H, 9.53; N, 14.72. Found: C, 75.81; H, 9.13; N, 14.87. IR (KBr) cm-1: 3398, 3184, 2948, 1643, 1606, 1454, 1302, 1101, 995, 795, 775, 698; 1 H NMR (200 MHz, CDCl3) delta: 1.35-1.65 (6H, m), 2.25-2.45 (4H, m), 3.38 (2H, s), 3.50-3.75 (2H, br), 6.57 (1H, brd, J=7.9 Hz), 6.65-6.75 (2H, m), 7.08 (1H, t, J=7.9 Hz).

Reference： [1]Patent: CN107698538,2018,A .Location in patent: Paragraph 0049-0051; 0054-0056
[2]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 179 - 190
[3]Patent: US6166006,2000,A

5
[ 77201-13-9 ]
[ 93138-55-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With titanium tetrachloride; magnesium In tetrahydrofuran at 0 - 20℃; Inert atmosphere;

Reference： [1]Zhang, Tongxin; Zhang, Yan; Zhang, Weixi; Luo, Meiming [Advanced Synthesis and Catalysis, 2013, vol. 355, # 14-15, p. 2775 - 2780]

6
[ 93138-55-7 ]
[ 73279-04-6 ]

Yield	Reaction Conditions	Operation in experiment
94.3%	With sulfuric acid; sodium nitrite; In water; at 0 - 85℃;	Add 1750 g of water to the reaction flask, cool to 10-15 °C, and add 500 g with stirring.(About 5.000 mol) concentrated sulfuric acid, controlled temperature below 30°C. After dropping,After cooling to 15° C., 475 g (2.50 mol) of Compound 7 prepared in Example 2 was added, and the mixture was stirred and completely dissolved. After cooling to 0° C. or lower, an aqueous solution containing 181 g (2.63 mol) of sodium nitrite was added dropwise.The temperature is controlled below 5°C.After completion of the dropwise addition, the incubation temperature is below 5°C for 0.5 hr. After TLC confirms that all reactions of compound 7 have been completed,Spare (stock solution 1).To another reaction flask was added 1250 g of water, and 375 g (about 3.75 mol) of concentrated sulfuric acid was added dropwise.After the dropwise addition was completed, heating was performed at a temperature of 75°C to 80°C. The stock solution 1 was added dropwise via a dropping funnel.The control temperature is 80 °C ± 5 °C. After the addition, securityThe reaction was carried out at a temperature of 80° C. to 85° C. for 6 hours to 8 hours, and the reaction was monitored by TLC. Until the diazonium salt disappears.After confirming the completion of the reaction, the reaction system is cooled to about 30°C.Then, 500 g of methanol was added, and about 1350 g (about 19.8 mol) of ammonia water was added dropwise, and the temperature was controlled below 60° C., and the pH was adjusted to be 9 to 10 (solids were precipitated during the alkalizing with ammonia).After the adjustment is completed, the system is cooled to 10° C. or less, and the crystallization is maintained for 3 to 4 hours. Filter, 60-80 °C blast drying. Light brown compound 1 was obtained with a dry weight of 450 g (theoretical amount: 477.45 g); yield: 94.3percent

Reference： [1]Patent: CN107698538,2018,A .Location in patent: Paragraph 0057-0060

7
[ 93138-55-7 ]
[ 78273-80-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium nitrite; sulfuric acid / water / 0 - 85 °C 2: potassium iodide; sodium hydroxide / dimethyl sulfoxide / 20 h / 100 - 110 °C 3: 80 - 165 °C

Reference： [1]Current Patent Assignee: INNER MONGOLIA JINGDONG PHARMACEUTICAL - CN107698538, 2018, A

8
[ 93138-55-7 ]
[ 93793-83-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sodium nitrite; sulfuric acid / water / 0 - 85 °C 2.1: potassium iodide; sodium hydroxide / dimethyl sulfoxide / 20 h / 100 - 110 °C 3.1: 80 - 165 °C 4.1: acetic acid / 2 h / Reflux 4.2: 0 - 5 °C

Reference： [1]Current Patent Assignee: INNER MONGOLIA JINGDONG PHARMACEUTICAL - CN107698538, 2018, A

9
[ 93138-55-7 ]
[ 586-96-9 ]
1-[3-(phenyldiazenyl)benzyl]piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With acetic acid In toluene at 60℃; Inert atmosphere;	4.3.7. 1-[3-(Phenyldiazenyl)benzyl]piperidine (m-4b) To a solution of commercial nitrosobenzene (100 mg,0.93 mmol) in anhydrous toluene (5 mL), 3-(piperidin-1-ylmethyl)aniline (178 mg, 0.93 mmol) and acetic acid (21 mL, 3.75 mmol)were added orderly under N2 and the reaction was stirred at 60 Covernight. The mixture was extracted with EtOAc, washed withwater and brine, dried with MgSO4, filtered and concentrated underreduced pressure. The residue was purified in reverse phase flashcolumn, from H2O to ACN. After lyophilization of the appropriatefractions diazene m-4b was obtained as orange oil (241 mg, 93%yield), with an (E)-isomeric purity >99%. 1H NMR (500 MHz,DMSO): d 7.90 (dd, J 6.6,1.5 Hz, 2H, Hm’’), 7.80 (t, J 1.5 Hz, 1H, Ho),7.78 (dt, J 7.7, 1.8 Hz, 1H, Ho’), 7.63e7.57 (m, 3H, Ho’’, Hp’), 7.54 (t,J 7.6 Hz, 1H, Hm’), 7.49 (dt, J 7.6, 1.4 Hz, 1H, Hp), 3.53 (s, 2H, Ha),2.39e2.31 (m, 4H, H2, H6), 1.50 (p, J 5.6 Hz, 4H, H3, H5), 1.40 (q,J 6.0 Hz, 2H, H4)13C NMR (126 MHz, DMSO): d 152.0 (Ci’), 151.9(Ci), 140.4 (Cm), 131.9 (Cp), 131.5 (Cp’), 129.5 (Co’’), 129.3 (Cm’), 122.5(Cm’’), 122.4 (Co), 121.5 (Co’), 62.4 (Ca), 53.9 (C2), 25.6 (C3), 24.0 (C4).HPLC-MS (15:95- g.t.10 min) tR 1.44 min, m/z 280.28 [MH] (Z)-isomer; 4.97 min, m/z 280.21 [MH] (E)-isomer. lmax 285,425 nm [(Z)-isomer]; 319 nm [(E)-isomer)]. HRMS [ESI] m/z 279.17353 [M], calcd for [C18H21N3] 279.17355.

Reference： [1]Herrera-Arozamena, Clara; Villalba-Galea, Carlos A.; de la Fuente Revenga, Mario; Estrada-Valencia, Martín; Martí-Marí, Olaia; Pérez, Concepción; Rodríguez-Franco, María Isabel [European Journal of Medicinal Chemistry, 2020, vol. 200]

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H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 93138-55-7 ] {[proInfo.proName]}

Quality Control of [ 93138-55-7 ]

Related Doc. of [ 93138-55-7 ]

Product Details of [ 93138-55-7 ]

Safety of [ 93138-55-7 ]

Application In Synthesis of [ 93138-55-7 ]

[ 93138-55-7 ] Synthesis Path-Upstream 1~2

[ 93138-55-7 ] Synthesis Path-Downstream 1~9

Precautionary Statements-General

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Physical hazards

Health hazards

Environmental hazards

Inquiry