Water → HCID 15035600, compound

Participants

Reaction Steps

To a stirred and cooled (ice-bath) amount of 200 ml of a boron tribromide solution in dichloromethane 1M was added dropwise a solution of 14.6 parts of 1,3-dihydro-1-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3-methyl-2H-imidazol-2-one in 665 parts of dichloromethane. Stirring was continued for 5 days at room temperature and then the reaction mixture was poured into a mixture of 200 parts of water, 158 parts of methanol and 180 parts of ammonium hydroxide. After stirring for 1 hour, the precipitate was filtered off, washed with dichloromethane and water and dried (=first fraction of product). The organic layer of the filtrate was separated and evaporated. The residue was triturated in dichloromethane. The solid was filtered off and dried (=second fraction). The two fractions were combined and crystallized from N,N-dimethylformamide, yielding 9.6 parts (68.5%) of 1,3-dihydro-1-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-3-methyl-2H-imidazol-2-one; mp. 283.1° C. (interm. 14).

Provenance & Evidence