Triethylamine → HCID 67974260, compound

HRID 1777507Notes

Reaction equation

HRID 1777507 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:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>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:28](=[O:29])[C:27]1[CH:31]=[CH:32][C:24]([CH2:23][Cl:22])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 701364-(Chloromethyl)benzoyl chlorideHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochloride

Product 1

HCID 67974260HCID 67974260, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.98 mL; 21.20 mmol) was added at 0° C. to a mixture of 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (2.0 g; 8.48 mmol) and 4-(chloromethyl)benzoyl chloride (1.74 g; 8.90 mmol) in dichloromethane (75 mL). The mixture was stirred for 1 hour 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 2.60 g (88%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-4-(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-2bf28d1e4d164e809fb7fc1954f5fae5
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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