Hydrochloric Acid → HCID 86744654, compound

HRID 358864Notes

Reaction equation

HRID 358864 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:13][CH3:14])[C:11]=1F)[N:8]([CH2:15][CH2:16][F:17])[CH:7]=[C:6]([C:18]([OH:20])=[O:19])[C:5]2=[O:21].[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.[ClH:29]>CS(C)=O.C(O)C>[ClH:29].[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:13][CH3:14])[C:11]=1[N:26]1[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]1)[N:8]([CH2:15][CH2:16][F:17])[CH:7]=[C:6]([C:18]([OH:20])=[O:19])[C:5]2=[O:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 531671-MethylpiperazineHCID 140718416,7-Difluoro-1-(2-fluoroethyl)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 86744654HCID 86744654, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

0.11 g (0.0004 mole) of 6,7-difluoro-1-(2-fluoroethyl)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (prepared as described in Preparation 15) and 0.20 g (0.002 mole) of N-methylpiperazine were dissolved in 3 ml of dimethyl sulfoxide, and the mixture was stirred at 70° C. for 6 hours. At the end of this time, the solvent and excess N-methylpiperazine were distilled off at the same temperature and under reduced pressure, and the residue was washed with ethyl acetate to give a pale-yellow powder. This powder was suspended in a mixture of 20 ml of ethanol and 1 ml of concentrated hydrochloric acid, and the suspension was concentrated by evaporation under reduced pressure. 20 ml of water were added to the residue, and the mixture was filtered to remove insoluble materials. The filtrate was concentrated by evaporation under reduced pressure to give 30 mg of 6-fluoro-1-(2-fluoroethyl)-8-methoxy-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride as a colorless powder melting at 270°-272° C. (with decomposition).

Workup

  1. distillationAt the end of this time, the solvent and excess N-methylpiperazine were distilled off at the same temperature and under reduced pressure
  2. washthe residue was washed with ethyl acetate
  3. customto give a pale-yellow powder
  4. concentrationthe suspension was concentrated by evaporation under reduced pressure
  5. addition20 ml of water were added to the residue
  6. filtrationthe mixture was filtered
  7. customto remove insoluble materials
  8. concentrationThe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-ee4b9cf454f04e448540aef97c246135
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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