Benzyl Chloride → N-Benzyl-3-acetyl-3-(4-chlorobenzyl)-piperidine

Participants

Reaction Steps

A suspension of 3-Acetyl-3-(4-Chlorobenzyl)-piperidine hydrochloride (0.7 g, 2.43 mmol) in acetonitrile (20 mL) was treated with solid sodium bicarbonate (200 mg, 4.8 mmol) and benzyl chloride (369 mg, 2.9 mol) and heated to reflux for 2 hours. The reaction was then cooled to room temperature, poured into saturated aqueous sodium bicarbonate (200 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated at reduced pressure. The residue was chromatographed on silica gel eluting with 2% methanol/chloroform to give 492 mg of the title compound. 1H NMR CDCl3 δ 7.40-7.25 (m, 5H), 7.22 (d,=8.5 Hz, 2H), 6.90 (d,=8.5 Hz, 2H), 3.45 (m, 2H), 3.00 (m, 1H), 2.80-2.50 (m, 3H), 2.20-1.90 (m, 4H), 2.00 (s, 3H), 1.60-1.50 (m, 2H), 1.30-1.10 (m, 1H).

Provenance & Evidence