Acetone → HCID 131716769, compound

Participants

Reaction Steps

A mixture of 188 parts of ethyl hexahydro-4-[[1-[(5-methyl-2-furanyl)methyl]-1H-benzimidazol-2-yl]-amino]-1H-azepine-1-carboxylate, 166.5 parts of potassium hydroxide, 18 parts of water and 1440 parts of 2-propanone was stirred for 18 hours at reflux temperature. After cooling, another portion of 166.5 parts of potassium hydroxide was added and stirring was continued for 6 hours at reflux. After cooling, the reaction mixture was evaporated and the residue was stirred in 1500 parts of water. The product was extracted three times with dichloromethane. The extract was dried, filtered and evaporated. The residue was converted into the (E)-2-butenedioate salt in 2000 parts of 2-propanone and 800 parts of ethanol. The reaction mixture was allowed to cool while stirring. The precipitated product was filtered off, washed with 2-propanone and crystallized from a mixture of 2-propanone and ethanol (1:2 by volume). The product was filtered off, washed with 2-propanone and dried in vacuo at 50° C., yielding 132.6 parts (52.9%) of N-(hexahydro-1H-azepin-4-yl)-1-[(5-methyl-2-furanyl)methyl]-1H-benzimidazol-2-amine (E)-2-butenedioate(2:3).trihydrate; mp. 115.2° C. (compound 48).

Provenance & Evidence