1-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 1-Ethyl-6-fluoro-7-[3-[(hexyloxy)methyl]-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 248509Notes

Reaction equation

HRID 248509 reaction equation
[CH2:1]([O:7][CH2:8][CH:9]1[CH2:14][NH:13][CH2:12][CH2:11][NH:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:15]([N:17]1[C:26]2[C:21](=[CH:22][C:23]([F:28])=[C:24](F)[CH:25]=2)[C:20](=[O:29])[C:19]([C:30]([OH:32])=[O:31])=[CH:18]1)[CH3:16]>N1C=CC=CC=1>[CH2:15]([N:17]1[C:26]2[C:21](=[CH:22][C:23]([F:28])=[C:24]([N:13]3[CH2:12][CH2:11][NH:10][CH:9]([CH2:8][O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:14]3)[CH:25]=2)[C:20](=[O:29])[C:19]([C:30]([OH:32])=[O:31])=[CH:18]1)[CH3:16]

Participants

4

Reactant 2

HCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 11298589HCID 11298589, compound

Product 1

HCID 148393921-Ethyl-6-fluoro-7-[3-[(hexyloxy)methyl]-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 3 g portion of 2-[(hexyloxy)methyl]piperazine was added to 20 ml of pyridine in a pressure bottle, under argon. A 1.26 g portion of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid was added, the bottle sealed and the mixture heated at 80°-90° C. for 4 hours, then evaporated. The residue was evaporated twice from toluene, the residue triturated with ether and the solid collected, giving 2.03 g of the desired product, mp 121°-124° C.

Workup

  1. customthe bottle sealed
  2. temperaturethe mixture heated at 80°-90° C. for 4 hours
  3. customevaporated
  4. customThe residue was evaporated twice from toluene
  5. customthe residue triturated with ether
  6. customthe solid collected

Sources & evidence

ORD record
ord-a9532f128a7142d890e94c694bc8e1ca
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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