Tetrahydrofuran → HCID 13769708, compound

Participants

Reaction Steps

To a stirred mixture of 1.95 parts of [2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-cyanamide, 45 parts of tetrahydrofuran and 50 parts of water was added a solution of 3.7 parts of 1-hydroxy-2-propanone in water (=50%). 5 Parts of a sodium hydroxide solution 2N were added dropwise. Upon completion, stirring was continued for 2 hours at room temperature. The reaction mixture was poured onto water. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 1.3 parts (6%) of 1-[(4-fluorophenyl)methyl]-N-[1-[2-[(4-methyl-2-oxazolyl)amino]ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 178.1° C. (compound 84).

Provenance & Evidence