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

HRID 1284503Notes

Reaction equation

HRID 1284503 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-oxo-3-quinolinecarboxylic 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 a high vacuum, 30 ml of water are added to the residue, the suspension is adjusted to pH 8 with 2N hydrochloric acid and the precipitate which has separated out is boiled up 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)-3-quinolinecarboxylic acid of decomposition point 234°-236° C. is obtained.

Workup

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

Sources & evidence

ORD record
ord-cd339c455c5343d1b96d0d7d20bd3ce5
Source dataset
uspto-grants-1986_01
Patent number
US04563459

Reaction notes

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