Thionyl Chloride → HCID 15925380, 화합물

참여 물질

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반응 단계

Thionyl chloride (3.6 cc) is added to a suspension, cooled to 5° C., of 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxylic acid hydrochloride (2.7 g) in methylene chloride (70 cc). The suspension is stirred for 3 hours at 25° C. and then concentrated to dryness at 30° C. under reduced pressure (30 mm Hg; 4 kPa) to give a yellow residue which is taken up with methylene chloride (50 cc) at 5° C. 3-Chlorobenzylamine (6.9 g) is added and the mixture is stirred for 12 hours at 25° C., and saturated sodium bicarbonate solution (150 cc) is then added. The mixture is extracted with ethyl acetate (2×100 cc). The organic phase is washed successively with distilled water (100 cc) and with brine (100 cc), dried over magnesium sulphate, filtered and concentrated to dryness at 40° C. under reduced pressure (30 mm Hg; 4 kPa) to give a brown oil which is purified by chromatography on a column (height: 30 cm; diameter: 2.5 cm) of silica (0.06-0.2 mm), eluting with methylene chloride (1 liter) and collecting 40-cc fractions. Fractions 12 to 24 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give a cream-coloured solid which is taken up in isopropyl ether (20 cc). The solid is separated by filtration, washed with isopropyl ether (2×5 cc) and dried at 40° C. under reduced pressure (1 mm Hg; 0.13 kPa). N-(3-Chlorobenzyl)-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide (2 g) is obtained in the form of a yellow solid, m.p. approximately 80° C.

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