Propargyl bromide → 8-[4-(2-propynyl)-1-piperazinyl]-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.8 g of 8-(1-piperazinyl)-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]-quinolizine 2-carboxylic acid hydrochloride hydrate, 0.4 ml of propargyl bromide, 0.8 ml of triethylamine and 10 ml of dimethylformamide was allowed to react by heating at 90° C. for 5 hours. After completion of the reaction insoluble substances were removed by filtration. After concentration under reduced pressure the filtrate was purified through a silica gel column chromatography (silica gel: Wako C-200, a trade name for a product of Wako Junyaku Co., Ltd.; eluent: chloroform-methanol (8:1 by volume)) to obtain 0.3 g of 8-[4-(2-propynyl)-1-piperazinyl]-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid as pale yellow rhombic crystals having a melting point of 211° to 213° C.

Provenance & Evidence