Hydrochloric Acid → (4-Tert-butyl-benzyl)-[2-(4-fluoro-3-trifluoromethyl-phenyl)-ethyl]-amine

Participants

Reaction Steps

A mixture of 4-tert-butylbenzaldehyde (0.62 mL, 3.69 mmol), 2-(4-fluoro-3-trifluoromethyl-phenyl)-ethylamine hydrochloride (600 mg, 2.46 mmol), and potassium carbonate (340 mg, 2.46 mmol) in methanol (7 mL) was stirred for 30 min at RT and subsequently refluxed for 2 h. After cooling to RT, sodium borohydride (140 mg, 3.69 mmol) was added and reaction mixture was refluxed for 3 h. After cooling, the reaction mixture was treated with 1 M aq. hydrochloric acid solution (0.5 M) at RT and concentrated. The residue was partitioned between water and ethyl acetate. After separation of the organic phase, the aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography (SiO2; ethyl acetate/heptane 1:4 then 1:2) to afford the title compound (784 mg, 90%). Light yellow oil, MS (ISP) 354.3 (M+H)+.

Provenance & Evidence