Diazabicyclo(2.2.2)octane → 1-Cyclopropyl-7-(3,5-dimethylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

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Reaction Conditions

Reaction Steps

A mixture of 2.8 g (0.01 mol) of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 1.14 g (0.01 mol) of cis-2,6-dimethylpiperazine and 2.2 g of diazabicyclo[2.2.2]octane is heated at 140° C. for 5 hours. The solvent is distilled off under high vacuum, 30 ml of water are added to the residue, the suspension is adjusted to pH 8 with 2N HCl and the precipitate which has separated out is extracted by boiling with 30 ml of methanol. 0.75 g (21% of theory) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3,5-dimethyl-1-piperazinyl)quinoline-3-carboxylic acid, of decomposition point 234°-236° C., is obtained. Mass spectrum: 359 (M+), 290, 289 (100%, M+ -70), 245,70.

Provenance & Evidence