Ethanol → HCID 19817095, compound

Participants

Reaction Steps

2-{3-[4-(4-Nitrophenyl)-1-piperazinyl]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (30 g), stannous chloride dihydrate (74.8 g) and ethanol (500 cc) are heated for one hour at 60° C. under a current of argon. Then sodium borohydride (1.3 g) is added over one hour in small portions. Stirring is continued for one hour at 60° C., then for 15 hours at a temperature of about 20° C. The mixture is poured into water and ice (500 cc) then alkalinized with 4N caustic soda to pH 9. The organic phase is extracted with diethyl ether (4×200 cc), absorbed in charcoal 3S (3 g), dried on anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (200 mm Hg; 2.7 kPa). The residue obtained in purified by recrystallization, first from boiling 1-propanol (250 cc), then twice from boiling ethanol (20 cc). 2-{3 -[4-(4-Aminophenyl)-1-piperazinyl] propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (2.4 g) is thus obtained, m.p. 113° C.

Provenance & Evidence