Triethylamine → N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(thiophen-2-yl)benzamide

HRID 925339

Reaction equation

HRID 925339 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH2:14].[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.C(N(CC)CC)C>ClCCl>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH:14][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([C:16]2[S:15][CH:19]=[CH:18][CH:17]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27763314-(2-Thienyl)Benzoyl ChlorideHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochloride

Product 1

HCID 67973188N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(thiophen-2-yl)benzamideYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(thiophen-2-yl)benzamide was obtained following Method C starting from 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.100 g, 0.424 mmol), 4-(thiophen-2-yl)benzoyl chloride (0.102 g; 0.445 mmol), and triethylamine (0.149 mL; 1.06 mmol) in dichloromethane (5 mL). Flash chromatography on silica gel (eluent 1 to 10% ethyl acetate in dichloromethane) furnished 0.058 g (36%) of N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(thiophen-2-yl)benzamide as a white solid.

Sources & evidence

ORD record
ord-1f0c46f3b93e4160ab31d17bfb9eb48f
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Linked notes

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