Sodium hydride → HCID 19817098, compound

Participants

Reaction Conditions

Reaction Steps

The experiment is carried out as in Example 18, starting with 5-chloronaphtho[1,8-cd]isothiazole 1,1-dioxide (1.2 g), sodium hydride (0.15 in an 80% dispersion in vaseline oil, 1-(3-chloropropyl)-4-phenyl 1,2,3,6-tetrahydropyridine (1.4 g), obtained as in Example 18, and dimethylformamide (30 cc). The reaction mixture is heated for one hour at 70° C., cooled to a temperature of about 20° C. then concentrated to dryness at 20° C. under reduced pressure (0.5 mm Hg; 0.07 kPa). The residue is redissolved in dichloromethane (100 cc) and the solution is washed with distilled water (50 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 a mixture of dichloromethane and ethyl acetate (90-10 vol) as eluant, and recrystallized from boiling acetonitrile (30 cc). 5-Chloro-2-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]naphtho[1,8-cd]isothiazole 1,1-dioxide (1 g) is obtained, m.p. 135° C.

Provenance & Evidence