Ethyl 1-benzylpiperidine-4-carboxylate → (1-Benzylpiperidin-4-yl)methanol

Participants

Reaction Steps

A solution of 1-benzyl-4-carboethoxypiperidine (74.3 g, 0.300 mole) in anhydrous Et2O (740 mL) was stirred at 0° C. under N2. Lithium aluminum hydride (11.4 g, 0.300 mole) was added in small portions over 0.5 hours. After an additional 2.5 hours, the reaction was carefully quenched with H2O (740 mL). The mixture was filtered through a Celite pad and rinsed with ethyl acetate (EtOAc), then the layers were separated. The aqueous layer was saturated with NaCl, then extracted with EtOAc (3×100 mL). The combined organics were extracted with brine, dried (MgSO4), and concentrated in vacuo. The resulting crude product was vacuum distilled, bp ~144° C. at 0.1 mm Hg, to yield the alcohol (55.8 g,91%) as a colorless, viscous oil. Analysis: Calculated for C13H19NO: C,76.06; H,9.33; N,6.82; found: C,75.87; H,9.16; N,6.55.

Provenance & Evidence