Dichloromethane → HCID 23001040, compound

Participants

Reaction Steps

To a solution of 4-(3-aminophenyl)-N-hexyl-4-n-propylpiperidine (Preparation 70, 25 mg, 0.08 mmol) in pyridine (0.5 ml) under nitrogen was added methanesulfonyl chloride (10 ml, 0.124 mmol) and the resultant mixture was stirred overnight. Ice (2 g) was added and, after 15 min, dichloromethane (3 ml) was added and the biphasic mixture was left to stir for 15 min. The layers were separated and the aqueous layer was extracted with dichloromethane (3 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by silica (5 g) column chromatography eluting with ethyl acetate:hexane:0.880 ammonia (60:40:1 to 80:20:1) to give the title compound as a colourless oil (28 mg, 92%). The free base was dissolved in diethyl ether (3 ml) and 1.1 mol equivalents of 1N ethereal hydrogen chloride solution was added to provide a precipitate. The solvent was decanted and the solid dried in vacuo to yield the title compound as a hygroscopic solid.

Provenance & Evidence