Riluzole → HCID 14674474, compound

Participants

Reaction Conditions

Reaction Steps

2-Amino-6-trifluoromethoxybenzothiazole (9.4 g) and N-(2-chloroethyl)piperidine hydrochloride (8.1 g) are heated for 1 hour to 130° C. Dimethylformamide (20 cc) is then added and the reaction is continued for 24 hours at 130° C. After cooling of the mixture to a temperature in the region of 20° C., the precipitate is filtered off and then treated with 1N sodium hydroxide (50 cc) in distilled water (100 cc). The residue obtained by extraction with dichloromethane, drying over magnesium sulphate and concentration to dryness under reduced pressure (20 mm Hg; 2.7 kPa) is purified by chromatography on a silica column, with ethyl acetate and then a mixture of ethyl acetate and methanol (95:5 by volume) as eluents. 2-Imino-3-(2-piperidinoethyl)-6-trifluoromethoxybenzothiazoline (2.9 g) is obtained in the form of a yellow oil, which is converted to a dihydrochloride subliming at about 200° C. after recrystallization in boiling absolute ethanol (20 cc).

Provenance & Evidence