1-Piperazinecarboxylic acid, ethyl ester → HCID 19911567, compound

Participants

Reaction Steps

To a stirred mixture of 13.5 parts of ethyl 1-piperazinecarboxylate and 160 parts of ethanol were added 18 parts of 2-(chloromethyl)-3H-imidazo[4,5-b]pyridine-3-ethanol. After the addition of 10.6 parts of sodium carbonate, the reaction mixture was stirred for 32 hours at reflux temperature. The whole was evaporated and the residue taken up in water. The product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 17.5 parts (62.7%) of ethyl 4-[[3-(2-hydroxyethyl)-3H-imidazo-[4,5-b]pyridin-2-yl]methyl]-1-piperazinecarboxylate; mp. 117.4° C. (compound 18).

Provenance & Evidence