Iodoethane → 8-fluoro-3-(3-ethoxy-3-methyl-1-butynyl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

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Reaction Steps

3.0 g (9.5 mmol) of 8-fluoro-4,5-dihydro-3-(3-hydroxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one were dissolved in 20 ml of N,N-dimethylformamide and treated at 3° with 2.97 g (19 mmol) of ethyl iodide and 2.13 g of freshly powdered potassium hydroxide (38 mmol). After stirring for 5 minutes the cooling bath was removed and the mixture was left to come to room temperature. The reaction mixture was then poured into 200 ml of water, acidified with 4N hydrochloric acid and extracted four times with methylene chloride. The combined extracts were washed five times with water, dried over magnesium sulphate and evaporated. By recrystallization of the crude product from ethyl acetate and hexane there was obtained 8-fluoro-3-(3-ethoxy-3-methyl-1-butynyl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 136°-138°.

Provenance & Evidence