Hydrochloric Acid → 4-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

4-(2-methylpiperidin-1-yl)-3-(trifluoromethyl)benzonitrile obtained in step 1 (28 g; 104.37 mmol) was dissolved in MeOH (280 mL) to which was added sodium hydroxide (336 mL; 5 M) and the reaction mixture was heated at 100° C. for 7 h. After this time, reaction mixture was cooled to 0° C. and acidified to pH ˜2 with HCl (5N). Product precipitated as a white solid that was filtered, washed with water and dried under vacuum to give the title compound as a white powder (27.50 g; 91%). 1H NMR (DMSO-d6) δ 13.30 (bs, 1H), 8.20-8.14 (m, 2H), 7.68 (d, J=8.2 Hz, 1H), 3.08 (m, 1H), 3.10-3.06 (m, 1H), 2.90-2.86 (m, 1H), 2.59-2.54 (m, 1H), 1.77-1.25 (m, 6H), 0.72 (d, J=6.0 Hz, 3H). HPLC (Method B) Rt 5.37 min (Purity: 99.8%). LC/MS (Method B): 288.2 (M+H)+.

Provenance & Evidence