3-(Dimethylamino)propyl chloride hydrochloride → 3-(3-[N,N-Dimethylamino]propylthio)-1-phenylindole hydrochloride

Participants

Reaction Steps

A suspension of the hydroidide salt from part (A) (27.0 g; 0.07M) in 2N aqueous sodium hydroxide (300.0 ml) was stirred under nitrogen and heated to reflux. After 10 minutes the mixture was cooled to 90° and solid 3-[dimethylamino]-propyl chloride hydrochloride (21.6 g; 0.14M) was added in small portions. A vigorous exothermic reaction occcurred and the solid dissolved. The solution was allowed to cool and was stirred at 20° for a further 17 hours. The resulting two-phase mixture was extracted with methylene chloride (3×100 ml.), and the combined organic extracts were washed with water (2×50 ml), dried (magnesium sulphate) and evaporated to give a viscous pale green oil. This was dissolved in 3.5N methanolic hydrogen chloride (50 ml.), evaporated and the residue was crystallised from acetonitrile (1200 ml.) to give the title compound as colourless leaflets, weight 11.3 g, m.p. 203°-7° (46.0% yield).

Provenance & Evidence