2-Methylpiperazine → Grepafloxacin

HRID 1081423Notes

Reaction equation

HRID 1081423 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:16])[C:10]([F:15])=[C:11](F)[CH:12]=3)[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[CH3:21][CH:22]1[CH2:27][NH:26][CH2:25][CH2:24][NH:23]1>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:16])[C:10]([F:15])=[C:11]([N:26]4[CH2:25][CH2:24][NH:23][CH:22]([CH3:21])[CH2:27]4)[CH:12]=3)[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 660572-MethylpiperazineHCID 146512541-Cyclopropyl-6,7-difluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 72474GrepafloxacinYield 43.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.75 g (2.68 mmol) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 1.07 g (10.4 mmol) of 2-methylpiperazine and 30 mL of acetonitrile was refluxed for 5 hours, then stirred at room temperature overnight. The precipitate was collected by filtration, washed with water/ethanol and acetonitrile, and dried in vacuo to give 0.42 g of the title compound, mp 189°-192° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water/ethanol and acetonitrile
  4. customdried in vacuo

Sources & evidence

ORD record
ord-02b4c4c3886b4f529632907ee15d4c93
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

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