Tetrahydrofuran → HCID 20222944, compound

Participants

Reaction Steps

To a stirred mixture of 0.8 parts of lithium aluminum hydride and 135 parts of tetrahydrofuran were added slowly 4 parts of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-1H-indol-3-acetamide. The whole was stirred and refluxed overnight. The reaction mixture was cooled in an ice bath and decomposed by the successive additions of 1 part of water, 4.5 parts of a sodium hydroxide solution 15% and 3 parts of water. The whole was filtered over Hyflo and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (96:4 by volume) saturated with ammonia, as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 1 part (25.5%) of 1-[(4-fluorophenyl)methyl]-N-[1-[2-[[2-(1H-indol-3-yl)ethyl]amino]ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 169.7° C. (compound 107).

Provenance & Evidence