1-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → (+)-1-Ethyl-6,8-difluoro-7-[3-(fluoromethyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 248531Notes

Reaction equation

HRID 248531 reaction equation
[F:1][CH2:2][CH:3]1[CH2:8][NH:7][CH2:6][CH2:5][NH:4]1.[CH2:9]([N:11]1[C:20]2[C:15](=[CH:16][C:17]([F:23])=[C:18](F)[C:19]=2[F:21])[C:14](=[O:24])[C:13]([C:25]([OH:27])=[O:26])=[CH:12]1)[CH3:10]>N1C=CC=CC=1>[CH2:9]([N:11]1[C:20]2[C:15](=[CH:16][C:17]([F:23])=[C:18]([N:7]3[CH2:6][CH2:5][NH:4][CH:3]([CH2:2][F:1])[CH2:8]3)[C:19]=2[F:21])[C:14](=[O:24])[C:13]([C:25]([OH:27])=[O:26])=[CH:12]1)[CH3:10]

Participants

4

Reactant 2

HCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 14479501HCID 14479501, compound

Product 1

HCID 14839398(+)-1-Ethyl-6,8-difluoro-7-[3-(fluoromethyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 55.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 650 mg of 2-(fluoromethyl)piperazine, 500 mg of 1-ethyl-1,4-dihydro-6,7,8-trifluoro-4-oxo-3-quinolinecarboxylic acid and 5 ml of pyridine was stirred under nitrogen in a capped bottle at for 2.5 hours. The solvent was removed and the residue triturated with methanol. The solid was collected, washed twice with methanol and dried, giving 376 mg of racemic 1-ethyl-6,8-difluoro-7-[3-(fluoromethyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxlic acid.

Workup

  1. customThe solvent was removed
  2. customthe residue triturated with methanol
  3. customThe solid was collected
  4. washwashed twice with methanol
  5. customdried

Sources & evidence

ORD record
ord-21b9a7a435d245c1896144e7e7efd765
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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