Chloroacetyl chloride → HCID 17985641, compound

Reaction equation

[Cl:1][CH2:2][C:3](Cl)=[O:4].C(N(C(C)C)CC)(C)C.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[CH2:24][NH:25][CH2:26][CH2:27][CH3:28])[CH:17]=[CH:16]1>C(Cl)Cl>[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[CH2:24][N:25]([CH2:26][CH2:27][CH3:28])[C:3](=[O:4])[CH2:2][Cl:1])[CH:17]=[CH:16]1

Participants

Procedure

Add chloroacetyl chloride (1.7 ml, 21.71 mmol) and diisopropylethylamine (10.38 ml, 62.04 mmol) to a solution of (1H-Indol-7-ylmethyl)propylamine (3.89 g, 20.68 mmol) in methylene chloride. Stir for 2 hours, quench with saturated aqueous ammonium chloride and extract into ethyl acetate. Wash the organic layers with saturated aqueous sodium chloride, dry over magnesium sulfate, filter, and concentrate under reduced pressure to yield N-(1H-indol-7-yl)methyl N-propyl 2-chloroacetamide (5.47 gm, 20.68 mMol).