Benzyl Chloride → Ethyl 1-benzylpiperidine-4-carboxylate

Participants

Reaction Steps

Ethyl isonipecotate (212 g, 1 35 mole), benzyl chloride (170 g, 1.35 mole), and potassium carbonate (322 g, 233 mole) were stirred at room temperature in absolute EtOH (1.8 L) for 72 hours. The crude mixture was filtered through Celite, rinsed with Et2O, and concentrated in vacuo. The resulting mixture was diluted with Et2O, and extracted with H2O (3×), then brine, dried (MgSO4), and concentrated in vacuo. The product was distilled under high vacuum, bp 128°-130° C. at 0.8 mm Hg, to yield 252 g of a colorless liquid (76%). Analysis: Calculated for C15H21NO2 : C,72.84; H,8.56; N,5.66; found: C,72.91; H,8.38; N,5.88

Provenance & Evidence