Triethylamine → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-(chloromethyl)benzamide

HRID 1777506Notes

Reaction equation

HRID 1777506 reaction equation
C(N(CC)CC)C.Cl.[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][CH2:20][NH2:21].[Cl:22][CH2:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](Cl)=[O:28]>ClCCl>[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][CH2:20][NH:21][C:27](=[O:28])[C:26]1[CH:30]=[CH:31][CH:32]=[C:24]([CH2:23][Cl:22])[CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27333243-(Chloromethyl)benzoyl chlorideHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochloride

Product 1

HCID 67974165N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-(chloromethyl)benzamideYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.93 mL; 13.78 mmol) was added at 0° C. to a mixture of 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (1.3 g; 5.51 mmol) and 3-(chloromethyl)benzoyl chloride (1.13 g; 5.79 mmol) in dichloromethane (75 mL). The mixture was stirred for 20 minutes at room temperature and was evaporated to dryness. The residue was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in dichloromethane) to furnish 1.45 g (76%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-(chloromethyl)benzamide as a white solid.

Workup

  1. customwas evaporated to dryness
  2. customThe residue was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-84061ab7482f4ac1969d990a9457b572
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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