Ethanol → N-(2-(7-Fluoro-1H-indol-3-yl)ethyl)-3-(2,2,3,3-tetrafluoropropoxy)benzylamine hydrochloride

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Reaction Steps

Add acetyl chloride (2.4 mL, 33.8 mmol) dropwise to anhydrous ethanol (50 mL) and stir the solution for 10 min at ambient temperature and add to a solution of N-(2-(7-fluoro-1H-indol-3-yl)ethyl)-3-(2,2,3,3-tetrafluoropropoxy)benzylamine (12.0 g, 30.1 mmol) in ethyl acetate. Concentrate the resulting solution under reduced pressure to give a yellow solid. Recrystallize the yellow solid from ethyl acetate/ethanol/diethyl ether to give the title compound: mp 142–143° C. MS(m/e): 399 (M+1), 397 (M−1). Calculated for C20H19F5N2O.HCl: Calcd: C, 55.24; H, 4.64; N, 6.44. Found: C, 55.44; H, 4.66; N, 6.46.

Provenance & Evidence