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rel-(2R,6S)-2,6-dimethylpiperazine → 3-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6-fluoro-4-oxo-, cis-

HRID 2050631
Notes
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Reaction equation

HRID 2050631 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6][N:7]2[CH:14]1[CH2:16][CH2:15]1.[CH3:21][C@H:22]1[CH2:27][NH:26][CH2:25][C@@H:24]([CH3:28])[NH:23]1>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:26]2[CH2:25][C@H:24]([CH3:28])[NH:23][C@H:22]([CH3:21])[CH2:27]2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6][N:7]2[CH:14]1[CH2:16][CH2:15]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

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Reactant 2

HCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 148802095-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 30788563-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6-fluoro-4-oxo-, cis-Yield 66.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 280 mg of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 542 mg of cis-2,6-dimethylpiperazine and 10 ml of pyridine was heated under reflux for 2.5 hours. The solvent was evaporated under reduced pressure. To the residue was added a 1N aqueous solution of sodium hydroxide, and the insoluble matter was removed by filtration. A 10% aqueous solution of acetic acid was added to the filtrate to adjust its pH to 8. The solution was then extracted with chloroform. The chloroform layer was dried with sodium sulfate, and concentrated under reduced pressure. Acetonitrile was added to the residue, and the mixture was cooled with ice. The crystals were collected by filtration, and recrystallized from aqueous ammonia to give 250 mg of 5-amino-1-cyclopropyl-6-fluoro-7-(cis-3,5-dimethyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. m.p. 253°-254° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. customThe solvent was evaporated under reduced pressure
  4. additionTo the residue was added a 1N aqueous solution of sodium hydroxide
  5. customthe insoluble matter was removed by filtration
  6. additionA 10% aqueous solution of acetic acid was added to the filtrate
  7. extractionThe solution was then extracted with chloroform
  8. dry with materialThe chloroform layer was dried with sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. additionAcetonitrile was added to the residue
  11. temperaturethe mixture was cooled with ice
  12. filtrationThe crystals were collected by filtration
  13. customrecrystallized from aqueous ammonia

Sources & evidence

ORD record
ord-313ac0b8780746f2943b2960c3c235d1
Source dataset
uspto-grants-1991_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05013841

Reaction notes

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