Hydrochloric Acid → (2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-{3-[3-(2-methylamino-ethyl)-phenoxy]-propyl}-amine hydrochloride salt

Participants

Reaction Steps

To a stirring solution of 2-(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-N-methyl-acetamide (101 mg, 0.17 mmol) (Intermediate 3 above) in anhydrous THF (10 mL) was added BH3 THF (0.34 ml, 1 M solution in THF). The resulting solution was then heated to reflux for 1.5 hours. Aqeous HCl (0.34 ml. 6 M) was then added to the reaction and the mixture was heated at reflux for 30 min. After cooling to RT, the reaction mixture was concentrated in vacuo and extracted with EtOAc (3×). The combined organic layers were washed with brine (1×), dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography over silica gel (silica gel 60, EM science) using 5% MeOH:dichloro-methane as eluent. The free base was dissolved in dichloromethane, 1 eq. of HCl (1M in Et2O) was added, and the mixture was evaporated to afford the title compound as a white solid (52 mg, 50%). MS(ES) m/e 581.4 (M+).

Provenance & Evidence