Sodium hydride → HCID 54378044, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 43.5 parts of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one and 270 parts of N,N-dimethylformamide are added portionwise 10 parts of sodium hydride dispersion 60%. After stirring for 1 hour at about 40°-50° C., there are added 53 parts of 3-(chloromethyl)-1-(phenylmethyl)pyrrolidine and the whole is stirred and heated overnight at about 110° C. The reaction mixture is cooled and poured onto water. The product is extracted with 4-methyl-2-pentanone. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is taken up in a diluted hydrochloric acid solution and the whole is stirred for 1 hour at room temperature. After cooling, the mixture is alkalized and the product is extracted with 4-methyl-2-pentanone. The extract is dried, filtered and evaporated. The residue is triturated in 2,2'-oxybispropane with activated charcoal. The latter is filtered off and the filtrate is allowed to crystallize. The product is filtered off and dried, yielding 40 parts (53%) of 1,3-dihydro-1-[1-(phenylmethyl)-3-pyrrolidinylmethyl]-2H-benzimidazol-2-one.

Provenance & Evidence