2-Bromoethanol → HCID 15925269, compound

Participants

Reaction Steps

A suspension of 10-[(2RS)-1-methylamino-2-propyl]-2-phenothiazinecarbonitrile (3.7 g), sodium hydrogen carbonate (1.6 g) and 2-bromoethanol (0.9 cc) in dimethylformamide (60 c ) is heated under reflux for 6 hours 15 minutes. After cooling, the mixture is concentrated to dryness under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C. The residue is taken up with ethyl acetate (100 cc), washed successively with distilled water (2×50 cc) and with saturated aqueous sodium chloride solution (50 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual orange oil (4.4 g) is purified by chromatography on a column (height: 35 cm; diameter: 2.6 cm) of silica gel (0.2-0.063 mm), eluting with a mixture (70:30 by volume) (1.25 liters) of ethyl acetate and cyclohexane and collecting 50-cc fractions. The combined fractions 9 to 22 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 10-{(2RS)-1-[N-methyl-N-(2-hydroxyethyl)amino]-2-propyl}-2-phenothiazinecarbonitrile (3.1 g) is thereby obtained in the form of a yellow oil.

Provenance & Evidence