Triethylamine → HCID 67974521, compound

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (0.111 mL; 1.52 mmol) was added to a mixture of 4-benzylbenzoic acid (0.100 g; 0.508 mmol) in chloroform (10 mL). The reaction mixture was stirred at 65° C. for 18 hours and evaporated to dryness. The resulting residue was dissolved in chloroform (6 mL) and the solution is cooled to 0° C. A solution of 2-(5-Chloro-1H-indol-3-yl)ethanamine hydrochloride (0.108 g; 0.457 mmol) and triethylamine (0.357 mL; 2.54 mmol) in chloroform (6 ml) was then added and the mixture was stirred for 30 minutes at room temperature. The volatiles were removed under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 1 to 20% ethyl acetate in dichloromethane) to furnish 0.155 g (78%) of 4-benzyl-N-(2-(5-chloro-1H-indol-3-yl)ethyl)benzamide as a white solid.

Provenance & Evidence