1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 15670693, compound

Participants

Reaction Steps

A mixture of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid(2.83 g), 3-acetamidomethylpiperidine (1.87 g) and triethylamine (1.5 g) inacetonitrile (60 ml) was refluxed with stirring for 6 hours. The precipitate was filtered to give 7-(3-acetamidomethylpiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (3.5 g). The product (3.0 g) was suspended in 6N hydrochloric acid (50 ml) and heated at 100° C. with stirring for 5 hours. The reaction mixture was concentrated in vacuum, and the crude material was dissolved in 20 ml of aqueous ammonium hydroxide under ice-cooling. Removal of the solvent followed by purification by silica gel column chromatography (chloroform:methanol:ammonium hydroxide=15:5:1) gave 7-(3-aminomethylpiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.6 g), which was recrystallized from methanol-water to afford colorless prisms. m.p. 242°-243° C.

Provenance & Evidence