Tetrahydrofuran → HCID 86744822, compound

Participants

Reaction Conditions

Reaction Steps

The experiment is carried out as in Exampe 1, starting with 2-(3-chloropropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (2.8 g), 4-hydroxy-4-(4-bromophenyl)piperidine (2.4 g) and sodium bicarbonate (0.94 g) in a mixture of dimethylformamide (80 cc) and tetrahydrofuran (50 cc). The mixture is heated for 5 hours to a temperature of about 100° C. then cooled to a temperature of about 20° C. Stirring is maintained for 15 hours at this temperature. After purification by flash-chromatography on a silica column, under a current of argon (0.5-1.5 bar) with a mixture of dichloromethane and methanol (95-5 vol) as eluant, and recrystallization from boiling ethyl acetate (50 cc), 2-(3-[4-(4-bromophenyl)-4-hydroxypiperidino]propylnaphtho[1,8-cd]isothiazole 1,1-dioxide (1.5 g) is obtained in the form of hydrochloride, of m.p. 110 C.

Provenance & Evidence