Diethyl Ether → HCID 53864197, compound

Participants

Reaction Steps

Triethylamine (0.62 ml) was added to a cloudy solution of (S)-4-(aminomethyl)-1-(7-chloro-1,4-benzodioxan-2-ylmethyl)piperidine (0.44 g) and 4-acetamidobenzenesulphonyl chloride (0.65 g) in dichloromethane (22 ml) under nitrogen. The resulting solution was stirred for 20 hours, diluted with dichloromethane (100 ml) and washed with water (100 ml) and brine (100 ml). After drying over anhydrous magnesium sulphate, the mixture was concentrated under reduced pressure to afford an orange oil. Purification by flash chromatography on silica gel eluting with a 15:1 mixture of dichloromethane and methanol gave an orange gum. Trituration with diethyl ether (20 ml) yielded (S)-(-)-4-acetamido-N-{[1-(7-chloro-1,4-benzodioxan-2-ylmethyl)-4-piperidyl]methyl}benzenesulphonamide as a pale orange solid (0.34 g); m.p. 173-176° C., [α]D22 -39.3° (c=0.37, MeOH).

Provenance & Evidence