Hydrochloric Acid → 4-[(2S)-2-methylpiperidin-1-yl]-3-(trifluoromethyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

4-[(2S)-2-methylpiperidin-1-yl]-3-(trifluoromethyl)benzonitrile (1.40 g; 5.22 mmol; 1 eq.) was dissolved in MeOH (7 mL) to which was added NaOH (5 N solution in water, 7 mL). The reaction mixture was heated to 100° C. for 7 hours. The reaction mixture was acidified to pH 2 with 5N HCl solution in water. The resulting precipitate was filtered and washed with water to give a light brown solid. It was recrystallized from Et2O/cHex to give a beige solid (851 mg; 57% over 2 steps). 1H NMR (DMSO-d6) δ 13.29 (s, 1H), 8.23-8.12 (m, 2H), 7.68 (d, J=8.4 Hz, 1H), 3.07 (m, 1H), 2.94-2.81 (m, 1H), 2.61-2.45 (m, 2H), 1.75 (m, 1H), 1.67-1.18 (m, 4H), 0.71 (d, J=6.1 Hz, 3H). HPLC (Method A), Rt 4.79 min (Purity: 99.9%). LC/MS (Method B): 286.2 (M+H)−; 288.0 (M+H)+.

Provenance & Evidence