7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 7-[3-[(Dimethylamino)methyl]-1-piperazinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 248458Notes

Reaction equation

HRID 248458 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[F:18].[CH3:19][N:20]([CH2:22][CH:23]1[CH2:28][NH:27][CH2:26][CH2:25][NH:24]1)[CH3:21]>N1C=CC=CC=1>[CH3:19][N:20]([CH2:22][CH:23]1[NH:24][CH2:25][CH2:26][N:27]([C:2]2[CH:11]=[C:10]3[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]3[CH2:12][CH3:13])=[CH:4][C:3]=2[F:18])[CH2:28]1)[CH3:21]

Participants

4

Reactant 2

HCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 14664185N,N-dimethyl-2-piperazinemethanamine

Product 1

HCID 148393477-[3-[(Dimethylamino)methyl]-1-piperazinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 15.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 480 mg of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 1.0 g of 2-dimethylaminomethylpiperazine and 5 ml of pyridine in a sealed flask flushed with argon was stirred at 120°-130° C. for 18 hours. The solvent was removed in vacuo. The residue was evaporated twice from toluene, giving a gum. The gum was added to a silica gel column and flash chromatographed with methanol:chloroform (1.5:8.5 saturated with water). Fractions 61 and 62 were combined, evaporated and dried, giving 105 mg of the desired product as a white solid, mp 148°-150° C.

Workup

  1. customflushed with argon
  2. customThe solvent was removed in vacuo
  3. customThe residue was evaporated twice from toluene
  4. customgiving a gum
  5. additionThe gum was added to a silica gel column and flash
  6. customchromatographed with methanol:chloroform (1.5:8.5 saturated with water)
  7. customevaporated
  8. customdried

Sources & evidence

ORD record
ord-243fa3f9efba4a93b2d8c9caaa49559e
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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