Benzene → 3-(aminocarbonyl)-N-(2,6-dichlorophenyl)-4-[2-hydroxy-3-(2-naphthalenyloxy)propyl]-1-piperazineacetamide dihydrochloride monohydrate

Participants

Reaction Steps

A mixture of 2.5 parts of [(2-naphthalenyloxy)methyl]oxirane, 3.31 parts of 3-(aminocarbonyl)-N-(2,6-dichlorophenyl)-1-piperazineacetamide, 45 parts of benzene and 20 parts of methanol was stirred first for 3 hours at room temperature and further for 30 hours at reflux. The reaction mixture was cooled and purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in 2-propanol and acetonitrile. Upon stirring overnight, the salt was filtered off and dried over week-end, yielding 1.39 parts (23%) of 3-(aminocarbonyl)-N-(2,6-dichlorophenyl)-4-[2-hydroxy-3-(2-naphthalenyloxy)propyl]-1-piperazineacetamide dihydrochloride monohydrate; mp. 155.3° C. (compound 69).

Provenance & Evidence