Propylamine → HCID 15925260, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 10-{(2RS)-1-[N-methyl-N-(1-methylethyl)amino]-2-propyl}-2-phenothiazinecarbothioamide hydrochloride (1.6 g) and propylamine (4.8 cc) in absolute ethanol (32 cc) is heated for 16 hours at a temperature in the region of 100° C. After cooling, the mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is dissolved in ethyl ether (100 cc) and the solution obtained is washed with N aqueous sodium hydroxide solution (4 cc) and then with saturated aqueous sodium chloride solution (2×10 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual red-brown gum is purified by chromatography on a column (height: 25 cm; diameter: 3 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa), eluting with a mixture (97:3 by volume) (1 liter) of methylene chloride and methanol and collecting 60-cc fractions. Fractions 6 to 12 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual yellow oil (0.85 g) is dissolved in ethyl ether (50 cc) in the presence of charcoal 3S. The mixture is filtered and a 3N solution (1 cc of hydrochloric acid in ethyl ether is added to the yellow filtrate, and the mixture is stirred for 1 hour at a temperature in the region of 20° C. The solid formed is drained washed with ethyl ether (5 cc) and dried under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C. 10-{(2RS)-1-[N-Methyl-N-(1-methylethyl)amino]-2-propyl}-N-propyl-2-phenothiazinecarbothioamide hydrochloride (0.58 g) is thereby obtained in the form of a yellow solid, m.p. about 140° C. (melts forming a a paste).

Provenance & Evidence