Reacción #456257

Ecuación de reacción

Triethylamine

(S)-4-(aminomethyl)-1-(7-bromo-1,4-benzodioxan-2-ylmethyl)piperidine

2,3-dichlorobenzenesulphonyl chloride

→

(S)-(-)-N-{[1-(7-bromo-1,4-benzodioxan-2-ylmethyl)-4-piperidyl]methyl}-2,3-dichlorobenzensulphonamide

Rendimiento 99.2%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with water (100 ml) and brine (100 ml)
2. 2
   Secadodried over anhydrous magnesium sulphate
3. 3
   Concentraciónconcentrated under reduced pressure
4. 4
   OtroPurification by flash chromatography on silica gel eluting
5. 5
   workup.ADDITIONwith a 9:1 mixture of dichloromethane and methanol

Procedimiento

Triethylamine (0.63 ml) was added to a solution of (S)-4-(aminomethyl)-1-(7-bromo-1,4-benzodioxan-2-ylmethyl)piperidine (0.5 g) and 2,3-dichlorobenzenesulphonyl chloride (0.74 g) in dichloromethane (15 ml) and stirred under nitrogen for 24 hours. The reaction was diluted with dichloromethane (100 ml), washed with water (100 ml) and brine (100 ml), dried over anhydrous magnesium sulphate and concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with a 9:1 mixture of dichloromethane and methanol gave (S)-(-)-N-{[1-(7-bromo-1,4-benzodioxan-2-ylmethyl)-4-piperidyl]methyl}-2,3-dichlorobenzensulphonamide as a cream solid (0.8 g) m.p. 93-95° C., [α]D22 -37.1°(c=0.93, MeOH).

Fuente