1H-Indole, 3-(4-piperidinylmethyl)- (9CI) → HCID 19898897, compound

Participants

Reaction Steps

A mixture of 4-(3-indolylmethyl)piperidine (0.4 g), 2-(2-chloroethyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (0.53 g), sodium hydrogen carbonate (0.17 g) and dimethylformamide (10 cc) is brought to reflux for 12 hours. After evaporation to dryness at 80° C. under reduced pressure (20 mm Hg; 2.7 kPa), the residue is taken up with water (30 cc) and extracted with ethyl acetate (2×50 cc). The combined organic phases are dried over magnesium sulphate and taken to dryness at 80° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is purified by flash chromatography on a silica column under a stream of nitrogen at moderate pressure (0.5-1.5 bar) with a dichloromethane/methanol mixture (99:1 by volume) as eluent. 2-{2-[4-(3-Indolylmethyl)piperidino]ethyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (0.4 g), m.p. 184° C., is obtained.

Provenance & Evidence