Triethylamine → 2-(2-Cyano-10-phenothiazinyl)propyl mesylate

Participants

Reaction Steps

Triethylamine (10 cc) is added with stirring to a solution, cooled to a temperature in the region of 5° C., of 10-(1-hydroxy-2-propyl)-2-phenothiazinecarbonitrile, L series (12.6 g) in methylene chloride (126 cc), a solution of methanesulphonyl chloride (5.6 cc) in methylene chloride (56 cc) is then added dropwise during 25 minutes, and stirring is continued for 1 hour 15 minutes at a temperature in the region of 10-15° C. The reaction mixture is washed successively with distilled water (2×100 cc) and with saturated sodium chloride solution (100 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40 C. 2-(2-cyano-10-phenothiazinyl)-1-propyl methanesulphonate, L series (16.2 g) is thereby obtained in the form of an orange oil.([α]20D =+29.9±0.3°; 2.4%; chloroform), which is used without further purification for the next stage of the synthesis.

Provenance & Evidence