Benzoyl chloride → HCID 11101390, compound

Participants

Reaction Steps

Benzoyl chloride (217 ml, 1.9 mmol) was added to a stirred solution of [2-(5-benzyloxy-1H-indol-3-yl)ethyl]dimethylamine (500 mg, 1.7 mmol), triethylamine (473 ml, 3.4 mmol) and 4-(dimethylamino)pyridine (20 mg, 0.2 mmol) in dry dichloromethane (5 ml) at 0° C. The reaction was allowed to warm slowly to ambient temperature, and stirred at this temperature overnight. The reaction was quenched with saturated aqueous sodium hydrogen carbonate. The aqueous was then extracted with dichloromethane (×3). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with dichloromethane/methanol/aqueous ammonia (80:8:1) to give the title compound (327 mg, 48%) is a thick oil. δH (250 MHz, CDCl3) 2.30 (6H, s), 2.52-2.60 (2H, m), 2.78-2.84 (2H, m), 5.16 (2H, s), 7.06-7.10 (3H, m), 7.30-7.64 (10H, m), 8.28 (0.5H, s), 8.32 (0.5H, s).

Provenance & Evidence