Trifluoroacetic acid → 1-{[3-(Trifluoromethyl)phenyl]methyl}piperidin-4-amine

Participants

Reaction Steps

A mixture of piperidin-4-ylcarbamic acid tert-butyl ester (2.5 g, 12.4 mmol), 3-(trifluoromethyl)benzyl bromide (1.7 ml, 11.3 mmol) and diisoproylethylamine (2.9 ml, 16.9 mmol) in dichloromethane (25 ml) was stirred at room temperature for 2 h. After this period, trifluoroacetic acid (32 ml) was added and the reaction mixture was stirred for a further 2 h. The solvent was evaporated in vacuo and a saturated solution of sodium carbonate was added. The mixture was extracted with dichloromethane and the separated organic layers were dried (Na2SO4), filtered, and the solvent evaporated in vacuo. The residue was purified by column chromatography (silica gel; 5-10% ammonia in methanol (7 M)/dichloromethane) to yield D6 (1.9 g, 60%) as a solid. C13H12F3N2 requires 258. Found 259 (MH+)

Provenance & Evidence