Diazabicyclo(2.2.2)octane → 3-Quinolinecarboxylic acid, 1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-
Reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].[CH3:20][C@H:21]1[CH2:26][NH:25][CH2:24][C@@H:23]([CH3:27])[NH:22]1.N12CCC(CC1)CN2>>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:25]4[CH2:24][CH:23]([CH3:27])[NH:22][CH:21]([CH3:20])[CH2:26]4)[CH:11]=3)[C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]2)[CH2:14][CH2:13]1Participants
4
Conditions
- Temperature
- 140 °C
Procedure
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.