Diethyl Ether → 1-(2-(4-Aminophenoxy)ethyl)-2-benzylpiperidine Dihydrobromide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-benzyl-1-(2-(4-nitrophenoxy)ethyl)piperidine hydrobromide (500 mg, 1.19 mmol) and Pd/C (10%, 50 mg, Aldrich) in MeOH (25 mL) was shaken under H2 (20-30 psi, Parr) for 2 h at 25° C. The catalyst was removed by filtration (Celite). The resulting solution was acidified with a dilute solution of HBr in MeOH (pH paper to red). The MeOH was removed in vacuo (rotoevaporator, 35-40° C.) to give a syrup. Ether (45 mL) was added and the resulting mixture was vigorously stirred at 25° C. for 24 h. A yellow suspension was obtained. The solid was collected, washed with ether (3×2 mL) and dried in vacuo (0.005 Torr, 56° C.) to give a beige powder (358 mg, 64%): mp 130° C.; 1H NMR (DMSO-d6) 1.28-1.95 (m, 6 H), 2.69-3.95 (m, 7 H), 4.60-4.55 (m, 2 H), 7.08-7.42 (m, 9 H), 9.60-10.25 (m, 4 H); HRMS Calcd for C20H26N20 : 310.2045. Found: 310.2040.

Provenance & Evidence