Acetic Acid → 4-[Methyl-(2-trifluoromethyl-phenyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

A mixture of 2-(methylamino)benzotrifluride (0.870 g, 5.000 mmol), 1-Boc-4-piperidone (1.500 g, 7.500 mmol)), acetic acid (1.5 mL, 17.5 mmol) and sodium triacetoxy borohydride (2.420 g, 11.000 mmol) in 1,2-dichloroethane (30 mL) was stirred at ambient temperature for 2 days. The reaction was quenched with water. The organic phase was separated and the aqueous phase was extracted with dichloromethane. The combined organic phase was washed with water, brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash chromatography to afford 4-[methyl-(2-trifluoromethylphenyl)amino]piperidine-1-carboxylic acid tert-butyl ester (0.360 g, 20%). 1H NMR (300 MHz, CDCl3) δ 7.58 (dd, J=1.2, 7.8 Hz, 1H), 7.48-7.14 (m, 3H), 4.08-4.00 (m, 2H), 2.95-2.87 (m, 2H), 2.68-2.58 (m, 5H), 1.72-1:67 (m, 1H).

Provenance & Evidence