HCID 13755070, compound → 3-(4-Methoxyphenyl)piperidine

Participants

Reaction Steps

To a solution of 1-benzyl-5-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine (1.5 g, 5.4 mmol) in 50 mL of methanol was added 10% Pd/C (1.14 g). Hydrogen gas was introduced via balloon and the reaction mixture was stirred overnight at rt. The reaction mixture was then filtered through Celite, and the filter pad was washed with additional methanol (100 mL). The filtrates were combined, and the methanol was evaporated under reduced pressure to give 3-(4-methoxyphenyl)piperidine (950 mg, 3.73 mmol, 69.4% yield). LCMS (Method 107): (ES-API), m/z 192.2 (M+H) RT=1.497 min; 1H NMR (300 MHz, DMSO-d6) δ 7.13 (dt, J=8.5, 2.0 Hz, 2H), 6.84 (dt, J=8.5, 2.2 Hz, 2H), 3.72 (s, 3H), 3.17 (s, 2H), 2.93 (d, J=10.6 Hz, 2H), 2.49-2.39 (m, 1H), 1.81 (d, J=1.9 Hz, 1H), 1.74-1.57 (m, 1H), 1.57-1.40 (m, 2H).

Provenance & Evidence