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

HRID 248460Notes

Reaction equation

HRID 248460 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]1[CH2:25][CH2:24][N:23]([CH2:26][CH:27]2[CH2:32][NH:31][CH2:30][CH2:29][NH:28]2)[CH2:22][CH2:21]1>N1C=CC=CC=1>[CH2:12]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([F:18])=[C:2]([N:31]3[CH2:30][CH2:29][NH:28][CH:27]([CH2:26][N:23]4[CH2:22][CH2:21][N:20]([CH3:19])[CH2:25][CH2:24]4)[CH2:32]3)[CH:11]=2)[C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8]1)[CH3:13]

Participants

4

Reactant 2

HCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 197635601-Methyl-4-(2-piperazinylmethyl)piperazine

Product 1

HCID 197635961-Ethyl-6-fluoro 1,4-dihydro-7-[3-[(4-methyl-1-piperazinyl)methyl]-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 425 mg portion of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 1.25 g of 1-methyl-4-(2-piperazinylmethyl)piperazine were suspended in 5 ml of pyridine and heated at reflux, under argon, for 18 hours. The solvents were removed and the residue evaporated twice from toluene. The residue was dissolved in dichloromethane, hexane was added, the resulting gum was separated, dissolved in dichloromethane and filtered. Ether was added to the filtrate, the resulting solid collected and recyrstallized, giving 360 mg of the desired product as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux, under argon, for 18 hours
  3. customThe solvents were removed
  4. customthe residue evaporated twice from toluene
  5. dissolutionThe residue was dissolved in dichloromethane
  6. additionhexane was added
  7. customthe resulting gum was separated
  8. dissolutiondissolved in dichloromethane
  9. filtrationfiltered
  10. additionEther was added to the filtrate
  11. customthe resulting solid collected

Sources & evidence

ORD record
ord-bbf6ca2307234e85a9ad1666e53ccea2
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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