Water → HCID 131716771, compound

Participants

Reaction Steps

To a stirred mixture of 85 parts of potassium hydroxide, 5 parts of water and 368 parts of 2-propanol were added 50.5 parts of ethyl [2-[hexahydro-4-[[1-[(5-methyl-2-furanyl)methyl]-1H-benzimidazol-2-yl]amino]-1H-azepin-1-yl]ethyl]carbamate (exothermic reaction, the mixture was cooled when the temperature reached 60° C.). The reaction mixture was refluxed for 2 hours. After cooling, the mixture was evaporated. The residue was taken up in 800 parts of water and the product was extracted three times with dichloromethane. The combined extracts were washed with a small amount of water, dried, filtered and evaporated. The residue was converted into the (E)-2-butenedioate salt in 320 parts of ethanol. The salt was filtered off, washed with ethanol and dried in vacuo at 40° C., yielding 48.0 parts (55.8%) of N-[1-(2-aminoethyl)hexahydro-1H-azepin-4-yl]-1-[(5-methyl-2-furanyl)methyl]-1H -benzimidazol-2-amine (E)-2-butenedioate(1:3); mp. ≥145° C. (compound 149).

Provenance & Evidence