Tetrahydrofuran → HCID 21251983, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6.84 parts of lithium aluminum hydride and 90 parts of tetrahydrofuran there was added a solution of 9 parts of intermediate 2 in 90 parts of tetrahydrofuran. After stirring for 2½ hour, there were added successively water and NaOH 15% while cooling on ice. The whole was filtered and the filtrate was evaporated. The residue was taken up in methylbenzene and this solution was dried, filtered and evaporated. The residue was heated at 200° C. for 10 min with 2 parts of urea. At 100° C., the whole was diluted with 25 parts of boiling water. The aqueous layer was decanted and the residue was treated with activated charcoal in a mixture of 35 parts of HCl (1N) and 35 parts of water. After filtration, the mixture was basified with NH4OH and the product was extracted with methylbenzene (80 parts and 40 parts). The combined extracts were dried, filtered and evaporated. The residue was crystallized from 4-methyl-2-pentanone and then converted into the monohydrochloride salt in methanol by addition of 2-propanol saturated with HCl. The salt was filtered off, recrystallized from water and dried, yielding 3.2 parts of 6-(phenylmethyl)-4,5,6,7-tetrahydroimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-one monohydrochloride; mp. 258.5-262° C. (comp. 1).

Provenance & Evidence