1-Bromo-3-chloropropane → N-(3-chloropropyl)piperidine hydrochloride

Participants

Reaction Steps

To a solution of piperidine (0.45 g, 5.3 mmol) and 1-bromo-3-chloropropane (5.2 g, 33 mmol) in toluene (17.5 mL) was added tetra-n-butylammonium hydrogensulfate (0.51 g, 1.5 mmol) and a 25% aqueous sodium hydroxide (10 mL), and the resulting mixture was stirred at 40° C. for 3 hours. The reaction solution was cooled to room temperature, and the toluene layer was separated and was then washed with a saturated aqueous sodium chloride and was dried over anhydrous sodium sulfate. After sodium sulfate was filtered off, hydrochloric acid/methanol (2 mL) was added to the filtrate and themixture was concentrated. The resulting crude crystals were recrystallized from methanol/ether to afford the title compound (0.96 g, yield: 91%) as white crystals.

Provenance & Evidence