Piperazine → 1-Cyclopropyl-6,8-difluoro-1,4-dihydro-5-methyl-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid

HRID 1081417Notes

Reaction equation

HRID 1081417 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:17])[C:10]([F:16])=[C:11]([N:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 146512581-Cyclopropyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 146511701-Cyclopropyl-6,8-difluoro-1,4-dihydro-5-methyl-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acidYield 87.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 0.85 g (2.85 mmol) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 1.00 g (11.6 mmol) of anhydrous piperazine, and 20 mL of acetonitrile was refluxed for 5 hours, then stirred at room temperature overnight. The precipitate was removed by filtration, washed with water and acetonitrile, and dried in vacuo to give 0.91 g of the title compound, mp 205°-206° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customThe precipitate was removed by filtration
  3. washwashed with water and acetonitrile
  4. customdried in vacuo

Sources & evidence

ORD record
ord-5bddf6eb7bac42d29f65cce21ea95e9c
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

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