Hydrochloric Acid → 1-[3-(Chloromethyl)benzoyl]piperidine

Participants

Reaction Steps

To an ice-cooled solution of piperidine (67.6 g, 0.793 mole) in tetrahydrofuran (1 L) was added dropwise a solution of 3-chloromethylbenzoyl chloride (100.0 g, 0.529 mmol). When the addition was complete, the reaction mixture was allowed to warm to ambient temperature and was left to stir overnight. The reaction mixture was poured into a solution of 1N hydrochloric acid. This solution was extracted with diethyl ether. The ether extracts were combined, washed with water, dried (MgSO4), and concentrated to afford 108.7 g (86%) of N-(3-(chloromethyl)benzoyl)piperidine (10) as a pale yellow oil whose 1H NMR in CDCl3 supported the structure.

Provenance & Evidence