4-Fluorobenzyl chloride → HCID 19848749, compound

Participants

Reaction Steps

To a solution of 5.0 g (23.2 mmole) of the 4-hydroxymethyl-piperidine-1-carboxylic acid t-butyl ester produced above, in 100 ml of dimethylformamide, was added 1.2 g (25.6 mmole) of a 50% sodium hydride oil dispersion. After stirring for 0.5 hours, 5.0 g (34.9 mmole) of 4-fluorobenzyl chloride was added, followed by a catalytic amount of tetrabutylammonium iodide. The suspension was stirred an additional 24 hours, quenched with saturated aqueous sodium chloride and extracted with ether. The organic layer was dried with magnesium sulfate and concentrated. The resulting oil was treated with methanolic hydrogen chloride for 4 hours. A white solid was obtained upon concentration, which was filtered and washed with hexane. 5.1 g of 4-(4-fluoro-benzyloxymethyl)-piperidine hydrochloride was obtained which had a melting point of 142°-145° C.

Provenance & Evidence