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

HRID 463697Notes

Reaction equation

HRID 463697 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]1

Participants

4

Reactant 3

HCID 136165Diazabicyclo(2.2.2)octaneHCID 483180Fluoroquinolonic acidHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

Product 1

HCID 4655521-Cyclopropyl-7-(3,5-dimethylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 21%

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.

Workup

  1. distillationThe solvent is distilled off under high vacuum, 30 ml of water
  2. additionare added to the residue
  3. customthe precipitate which has separated out
  4. extractionis extracted

Sources & evidence

ORD record
ord-b44c75d807284a9788ff9c1ea06ef7d3
Source dataset
uspto-grants-1985_10
Patent number
US04544658

Reaction notes

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