Hydrochloric Acid → (+/-)-Methyl(cis)-2-[4-(trifluoromethyl)phenyl]piperidine-4-carboxylate hydrochloride

Participants

Reaction Steps

Methyl 2-[4-(trifluoromethyl)phenyl]isonicotinate (5 g) was dissolved in MeOH (180 ml) and HCl in dioxane (4.5 ml, 4N). To this solution was added platinum oxide (500 mg) and the mixture was hydrogenated at 30 psi for 2 h. The mixture was filtered through Hyflo® to remove the catalyst and the solution was evaporated and azeotroped with toluene to yield the product as a white crystalline solid (5 g). 1H NMR (400 MHz, CDCl3) δ: 1.95-2.03 (1H, m), 2.09-2.17 (1H, m), 2.33 (1H, d, J 14.5), 2.44 (1H, d, J 14.2), 2.95-3.02 (1H, m), 3.35-3.39 (1H, m), 3.60-3.64 (1H, m), 3.75 (3H, s), 4.51 (1H, dd, J 2.7, 12.6), 7.74 (2H, d, J 8.2), 7.83 (2H, d, J 8.2); M/Z (ES+) 288 (MH+).

Provenance & Evidence