4-tert-Butylbenzaldehyde → (4-Tert-butyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine

Beteiligte Stoffe

Reaktionsschritte

A solution of 4-tert-butylbenzaldehyde (0.38 mL, 2.25 mmol) and 2-(3-trifluoromethyl-phenyl)-ethylamine (0.24 mL, 1.50 mmol) in methanol (4.5 mL) was stirred for 30 min at RT and subsequently refluxed for 4 h. After cooling, sodium borohydride (85 mg, 2.25 mmol) was added at RT, then after stirring for 5 min the reaction mixture was refluxed for 4 h. After cooling down to RT, the reaction mixture was treated with 1 M aq. hydrochloric acid solution (4 drops) and concentrated. The residue was dissolved in water/ethyl acetate. After separation of the organic phase, the aqueous phase was extracted with ethyl acetate, 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 1:2) to afford the title compound (450 mg, 89%). Colorless viscous oil, MS (ISP) 336.3 (M+H)+.

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