Water → HCID 13769773, compound

Participants

Reaction Steps

To a stirred mixture of 6.76 parts of 1-[(4-fluorophenyl)methyl]-N-[1-[2-(2-thiazolylamino)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine, 1.5 parts of N,N-diethylethanamine and 225 parts of trichloromethane was added dropwise a solution of 2.1 parts of benzoyl chloride in trichloromethane. Upon completion, stirring was continued overnight. The reaction mixture was poured into water. The layers were separated. The organic layer 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 2,2'-oxybispropane and 2-propanone. The product was filtered off and dried, yielding 4 parts (48%) of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-N-(2-thiazolyl)benzamide; mp. 155.9° C. (compound 100).

Provenance & Evidence