Piperazine → 3-Quinolinecarboxylic acid, 1,4-dihydro-1-(1,1-dimethylethyl)-6-fluoro-4-oxo-7-(1-piperazinyl)-

HRID 1031554Notes

Reaction equation

HRID 1031554 reaction equation
[CH3:1][C:2]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([F:16])=[C:12](Cl)[CH:13]=2)[C:8](=[O:17])[C:7]([C:18]([OH:20])=[O:19])=[CH:6]1)([CH3:4])[CH3:3].[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>N1C=CC=CC=1>[CH3:1][C:2]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([F:16])=[C:12]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[CH:13]=2)[C:8](=[O:17])[C:7]([C:18]([OH:20])=[O:19])=[CH:6]1)([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 14839592HCID 14839592, compound

Product 1

HCID 1228323-Quinolinecarboxylic acid, 1,4-dihydro-1-(1,1-dimethylethyl)-6-fluoro-4-oxo-7-(1-piperazinyl)-Yield 42.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.3 g (1.01 mmole) 1-(1,1-dimethylethyl)-6-fluoro-7-chloro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 0.3 g (3.48 mmoles) piperazine in 1 mL pyridine was heated under reflux for 18 hours. After cooling the mixture was concentrated under reduced pressure. The residue was poured in 10 mL of 10% acetic acid. After filtration of little insoluble the solution was taken to pH 6.5, saturated with brine and extracted three times with dichloromethane. After evaporation the resulting solid obtained was purified in water to give 0.15 g of 1-(1,1-dimethylethyl)-1,4-dihydro-6-fluoro-7-piperazinyl-4-oxo-3-quinolinecarboxylic acid purified as in method 1.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. temperatureAfter cooling the mixture
  4. concentrationwas concentrated under reduced pressure
  5. additionThe residue was poured in 10 mL of 10% acetic acid
  6. filtrationAfter filtration of little insoluble the solution
  7. extractionextracted three times with dichloromethane
  8. customAfter evaporation the resulting solid
  9. customobtained
  10. customwas purified in water

Sources & evidence

ORD record
ord-6bd0372788144910a050c3bb15a5afb6
Source dataset
uspto-grants-1990_09
Patent number
US04954507

Reaction notes

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