Ethylene Glycol → HCID 131716474, compound

Participants

Reaction Steps

A mixture of 105 parts of ethyl 4-[[1-(2-ethoxyethyl)-1H-benzimidazol-2-yl]amino]hexahydro-1H-azepine-1-carboxylate, 79 parts of potassium hydroxide and 833 parts of 1,2-ethanediol was stirred overnight at reflux temperature. The reaction mixture was distilled in vacuo and the residue was taken up in dichloromethane. The organic phase was filtered and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt. The salt was filtered off and crystallized from 2-propanol. The product was filtered off and dried, yielding 16.4 parts (9.9%) of 1-(2-ethoxyethyl)-N-(hexahydro-1H-azepin-4-yl)-1H-benzimidazol-2-amine ethanedioate(1:3), monohydrate (compound 37).

Provenance & Evidence