Sodium hydride → HCID 14580056, compound

Participants

Reaction Conditions

Reaction Steps

The experiment is carried out as in Example 18, starting with 6-chloronaphtho[l,8-cd]isothiazole 1,1-dioxide (1.4 g), 1-(3-chloropropyl)-4-(4-fluorophenyl)piperazine (1.5 g), sodium hydride (0.18 g) in an 80% dispersion in vaseline oil and dimethylformamide (15 cc). The reaction mixture is heated for 1 hour 30 minutes at 90° C., cooled to a temperature of about 20° C. and then concentrated to dryness at 60° C. under reduced pressure (0.5 mm Hg; 0.07 kPa). The residue is redissolved in dichloromethane (50 cc) and the solution is washed with distilled water (20 cc), dried over magnesium sulphate and concentrated to dryness at 20° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is purified by chromatography on a silica column with mixture of dichloromethane and ethyl acetate (95-5 vol) as eluant, then recrystallized from boiling acetonitrile (10 cc). 6-Chloro-2-{3-[4-(4-fluorophenyl)-l-piperazinyl]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (1.2 is obtained, m.p. 125° C.

Provenance & Evidence