Dimethylformamide → 2-{3-[4-(4-Methylphenyl)-4-hydroxypiperidino]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide

Participants

Reaction Conditions

Reaction Steps

The experiment is carried out as in Example 1, starting with 2-(3-chloropropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (2,8 g), 4-hydroxy-4-(4-methylphenyl)piperidine (2.1 g) and sodium bicarbonate (0.94 g) i mixture of dimethylformamide (60 cc) and tetrahydrofuran (50 cc). The mixture is heated for 5 hours at 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 at medium pressure (0.5-1.5 bar) with a mixture of dichloromethane and methanol (95-5 vol) as eluant, 2-{3-[4-(4-methylphenyl)-4-hydroxypiperidino ]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (1 g) is obtained, in the form of 1,1-dioxide (1 g) is obtained, in the form of the hydrochloride of m.p. 218° C.

Provenance & Evidence