Piperazine → 8-Fluorociprofloxacin

HRID 978203Notes

Reaction equation

HRID 978203 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)[C:12]=3[F:14])[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 4837PiperazineHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 1228488-FluorociprofloxacinYield 54.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1.00 g (3.53 mmol) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 10.0 ml of acetonitrile and 0.54 g (3.53 mmol) of 1,8-diazobicyclo[5.4.0]undec-7-ene, was added 1.70 g (19.7 mmol) of piperazine. The mixture was refluxed for one hour and then stirred overnight. It was concentrated, dissolved in ammonium hydroxide and filtered. The filtrate was then concentrated to one-half volume and filtered to give 0.67 g of the title compound, mp >270° C.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. concentrationIt was concentrated
  3. dissolutiondissolved in ammonium hydroxide
  4. filtrationfiltered
  5. concentrationThe filtrate was then concentrated to one-half volume
  6. filtrationfiltered

Sources & evidence

ORD record
ord-986c88cacfae4eb0b95dc5aafbb1b84c
Source dataset
uspto-grants-1987_05
Patent number
US04663457

Reaction notes

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