Piperazine → 5-Amino-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid

HRID 1110725Notes

Reaction equation

HRID 1110725 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([Cl:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>C(#N)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[C:9]([Cl:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 148965465-Amino-8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

Product 1

HCID 148965765-Amino-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acidYield 96.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1.57 g (5.00 mmol) of 5-amino-8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3quinolinecarboxylic acid in 20 ml of acetonitrile was added 1.7 g (20.0 mmol) of piperazine. The mixture was refluxed for four hours, cooled, filtered, and washed with acetonitrile to give 1.83 g of the title compound.

Workup

  1. temperatureThe mixture was refluxed for four hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washwashed with acetonitrile

Sources & evidence

ORD record
ord-fb7f00bc83264f50982a6437cb5fbaa7
Source dataset
uspto-grants-1990_12
Patent number
US04977154

Reaction notes

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