Methyl iodide → 4,5-dihydro-3-(3-methoxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Participants

Reaction Steps

4.58 g (80 mmol) of freshly powdered potassium hydroxide was suspended in 65 ml of dimethyl sulfoxide and cooled to 5°. 5.67 g (19.2 mmol) of 4,5-dihydro-3-(3-hydroxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one and 5.47 g (38.5 mmol) of methyl iodide were added thereto in succession. The cooling bath was removed and the mixture was stirred for a further 1 hour. The reaction mixture was evaporated and the residue was chromatographed on silica gel while eluting with methylene chloride/methanol (19.5:0.5). After crystallization from tert.-butyl methyl ether there was obtained 4,5-dihydro-3-(3-methoxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 136°-137°.

Provenance & Evidence