Dimethylamine → HCID 14726796, compound

Participants

Reaction Conditions

Reaction Steps

2-(2-Bromo-3-[4-(4-fluorophenyl)-1-piperazinyl]propyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (4.2 g), triethylamine (1.1 cc) and dimethylamine (0.5 cc) in toluene (50 cc) are introduced into a 250 cc bomb ap paratus cooled to a temperature of about 0° C. The mixture is stirred and heated for 8 hours to a temperature close to 120° C., then cooled to a temperature of about 20° C. Stirring is continued for 15 hours at this temperature, then the reaction mixture is concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residual oil is purified by flash-chromatography on a silica column, under a current of argon at medium pressure (0.5-1.5 bar) with ethyl acetate as eluant. After recrystallization from boiling acetonitrile (15 cc), 2(2-dimethylamino-3-[4-(4-fluorophenyl)-1-piperazinyl]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (1.9 g) is obtained, m.p. 118° C. 2-(2-Bromo-3-[4-(4-fluorophenyl)-1-piperazinyl]propyl}naphtho[ 1,8-cd]isothiazole 1,1-dioxide may be prepared in the following manner: phosphorus tribromide (1 cc) is poured into 2-{3-[4-(4-fluorophenyl)-1-piperazinyl]-2-hydroxypropyl}naphtho[1,8-cd]isothiazole 1,1dioxide (11.5 g) in toluene (150 cc). The mixture is heated at boiling point for 4 hours, then is cooled to a temperature of about 20° C. The reaction mixture is redissolved in distilled water (300 cc) and alkalinized to pH 11 with N caustic soda (20 cc). The organic phase is extracted with dichloromethane (4×300 cc), dried centrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residual oil is purified by flash-chromatogra-phy on a silica column, under a current of argon at medium pressure (0.5-1.5 bar) with ethyl acetate as diluent. 2-(2-Bromo-3-[4-(4-fluorophenyl)-1-piperazinyl]pripyl}naptho[1,8j-cd]isothiazole 1,1-dioxide (5.7 g) is obtained, m.p. 102° C, which is used in the crude state in the subsequent syntheses.

Provenance & Evidence