Triethylamine → HCID 14502148, compound

Participants

Reaction Conditions

Reaction Steps

Triethylamine (8.4 cc) is added to a solution of ethyl 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboximidate dihydrochloride (13.63 g) in absolute ethanol (150 cc), and the reaction mixture is diluted with dry ethanol (100 cc). Gaseous ammonia is bubbled for 4 hours into the reaction mixture, which is then stirred for 12 hours at 25° C. The suspension obtained is filtered on sintered glass and the filtrate is concentrated to dryness at 25° C. under reduced pressure (30 mm Hg; 4 kPa) to give a yellow product of meringue-like consistency, which is purified by chromatography on a column of alumina (height: 23 cm; diameter: 4 cm), eluting with mixtures of methylene chloride and methanol in proportions of 95:5 (750 cc) and 50:50 (1,500 cc) and collecting 125-cc fractions. The first 900 cc of eluate are discarded and fractions 8 to 11 are combined and concentrated to dryness at 25° C. under reduced pressure (30 mm Hg; 4 kPa) to give 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamidine hydrochloride (4.5 g) in the form of a yellow product of meringue-like consistency.

Provenance & Evidence