4-benzylpiperidine-1-carbonyl chloride

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Benzylpiperidine (0.5 g, 2.86 mmol) was added to a mixture of phosgene (3.8 ml of 20% phosgene in toluene solution, 7.13 mmol). The mixture was stirred at 0° C. for 1 hour. The reaction mixture was partitioned between water (25 ml) and ethyl acetate (2×25 ml). The organic phase was washed with 1N HCl (1×40 ml), saturated sodium chloride (1×50 ml), dried over sodium sulfate and concentrated to give a yellow oil. Purification by flash column chromatography (silica gel, 0-10% ethyl acetate/hexane) gave 0.47 g of title product. IR (film) 1733.1 cm−1. The reaction mixture was partitioned between water (25 ml) and ethyl acetate (2×25 ml) The organic phase was washed with 1N HCl (1×40 ml), saturated sodium chloride (1×50 ml) dried over sodium sulfate concentrated to give a yellow oil Purification by flash column chromatography (silica gel, 0-10% ethyl acetate/hexane)