1,2-Diaminocyclohexane → HCID 15925359, compound

Participants

Reaction Conditions

Reaction Steps

1,2-Diaminocyclohexane (9.3 g) is added to an ethanolic solution (35 cc) of 10-[(2RS)-1-dimethylamino-2-propyl]-2-phenothiazinecarbothioamide (2.8 g). The mixture is heated in an autoclave to 160° C. for 4.5 hours. The reaction mixture is diluted with ethyl acetate (100 cc) and washed with distilled water (3×100 cc). The organic phase is separated after settling has taken place, dried over magnesium sulphate, filtered and evaporated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is purified by chromatography on a column (height: 22 cm; diameter: 4 cm) of silica gel (0.04-0.06 mm) with a slight excess pressure of nitrogen (40 kPa), eluting with 1,2-dichloroethane (1 liter) and mixtures of 1,2-dichloroethane and methanol in proportions (by volume) of 90:10 (3 liters), 80:20 (2 liters), 70:30 (2 liters) and 50:50 (1 liter) and with pure methanol (1 liter) and collecting 125-cc fractions. Fractions 63 to 80 containing the pure product are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give 10-[(2RS)-1-dimethylamino-2-propyl]-2-(3a,4,5,6,7,7a-hexahydro-1H-benzimidazol-2-yl)phenothiazine (1.2 g) in the form of a yellow product of meringue-like consistency.

Provenance & Evidence