Hydrogen Sulfide → HCID 54318968, compound

Participants

Reaction Conditions

Reaction Steps

1,2-Diaminocyclohexane (7.98 g) is added to an ethanolic solution (30 cc), saturated with hydrogen sulphide, of 10-{1-[(2R)-2-hydroxymethyl-1-pyrrolidinyl]-2-propyl}-2-phenothiazinecarbothioamide, L series (2.79 g). The mixture is heated in an autoclave at 150° C. for 17 hours, then diluted with ethyl acetate (250 cc) and washed with distilled water (4×200 cc). The organic phase is separated after settling has taken place, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is stirred with boiling acetonitrile (6×30 cc), and the oil obtained is solidified by stirring with isopropyl ether (100 cc). The residue is chromatographed on a column (height: 52 cm; diameter: 2.5 cm) of silica gel (0.2-0.06 mm), eluting with a 60:40 (by volume) mixture (2 liters) of 1,2-dichloroethane and methanol and collecting 120-cc fractions. The first liter is discarded, and fractions 4 to 7 containing the pure product are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give 2-(3a,4,5,6,7,7a-hexahydro-1H-benzimidazol-2-yl)-10-{1-[(2R)-2-hydroxymethyl-1-pyrrolidinyl]-2-propyl}phenothiazine, L series (1.8 g) in the form of a yellow solid.

Provenance & Evidence