Diethyl Ether → HCID 23294462, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-benzyl-1-(2-(4-nitrophenoxy)ethyl)piperidine hydrobromide (900 mg, 2.14 mmol) and Pd/C (10%; 100 mg) in MeOH (50 mL) was shaken under H2 (20-30 psi, Parr) for 2.25 h at 25° C. The catalyst was removed by filtration (Celite). The resulting solution was acidified with a dilute solution of HBr in MeOH. The MeOH was removed in vacuo (rotoevap) to give a syrup. Ether (45 mL) was added and the resulting mixture was vigorously stirred at 25° C. for 48 h. A gray suspension was obtained. The solid was collected, washed with ether (3×3 mL) and dried in vacuo (0.005 Torr, 56° C.) to give a beige powder (606 mg, 60%): mp>130° C.; 1H NMR (DMSO-d6) 1.33-1.88 (m, 5 H), 2.38-3.75 (m, 8 H), 4.25-4.45 (m, 2 H), 7.04-7.38 (m, 9 H), 9.49-10.30 (m, 4 H).

Provenance & Evidence