Trifluoroacetic acid → 4-(4-Chlorophenyl)piperidine

Participants

Reaction Steps

Into a 250-mL round-bottom flask, was placed a solution of tert-butyl 4-(4-chlorophenyl)piperidine-1-carboxylate (compound 42.3, 5.00 g, 16.9 mmol) in dichloromethane (100 mL), trifluoroacetic acid (9.6 g, 84 mmol). The resulting solution was stirred overnight at room temperature and then concentrated under reduced pressure. The residue was carefully diluted with ethyl acetate (100 mL) and aqueous sodium bicarbonate was added until a pH of 8 was attained. The resulting mixture was washed with brine (100 mL) and the organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure to yield the title compound as a light yellow solid (2.30 g, 70%).

Provenance & Evidence