Hydrochloric Acid → HCID 86734370, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethanethiol (1.49 ml.) in dry dimethylformamide (30 ml.) in an atmosphere of nitrogen is treated portionwise with sodium hydride (800 mg. of a 60% dispersion in mineral oil), with stirring at 20°-25° C. After 15 mins. the internal temperature is raised to 100° C. and the 4-methoxy-1'-allylthioxanthene-9-spiro-4'-piperidine (1.685 g.) is added in one portion. The solution is heated at 100° C. for 45 mins., cooled to ambient temperature, poured into water (300 ml.), acidified with concentrated HCl, the mixture filtered and the filtrate rebasified with solid sodium carbonate and extracted three times with ethyl acetate. The combined ethyl acetate extracts are washed with water, dried over MgSO4 and then evaporated, to give 4-hydroxy-1'-allylthioxanthene-9-spiro-4'-piperidine m.p. 224° C. on recrystallisation from methanol/dimethylformamide/water.

Provenance & Evidence