Benzyl Chloride → Ethyl 1-benzylpiperidine-4-carboxylate

Participants

Reaction Steps

A mixture of ethyl isonipecotate (212 g, 1.35 mol), benzyl chloride (170 g, 1.35 mol) and potassium carbonate (322 g, 2.33 mol) in absolute ethanol (1.8 L) was stirred mechanically at room temperature for 72 h. Solvent was removed in vacuo and the residue was dissolved in water and then extracted with ether three times. The combined organic layers were dried over magnesium sulfate, filtered and solvent was removed in vacuo to give a pale yellow oil. Vacuum distillation (b.p. 134°-136° C., 1.0 Torr) gave a colorless liquid (252 g, 76% yield): 'H-NMR: 7.30-7.22 (m, 5H), 4.12 (q, 2H, J=7), 3.48 (s, 2H), 2.88-2.82 (m, 2H), 2.33-2.19 (m, 1H), 2.08-1.67 (m, 6H), 1.24 (t, 3H, J=7); Anal.: Calcd. for C15H21NO2 : C,72.84, H,8.56, N,5.66; Found: C,72.91, H,8.38, N,5.88.

Provenance & Evidence