Piperazine → Ciprofloxacin

HRID 466251Notes

Reaction equation

HRID 466251 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11](F)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1.[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 2764CiprofloxacinYield 95.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

26.5 parts by weight of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are introduced into a solution of 26.7 parts by weight of piperazine in 200 parts by volume of water, which is heated to reflux. The mixture is kept under reflux for 90 minutes and then cooled. The precipitate is separated off, washed with water and dried. 31.5 parts by weight (95.2% of theory) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid are obtained.

Workup

  1. temperatureis heated to reflux
  2. temperatureunder reflux for 90 minutes
  3. temperaturecooled
  4. customThe precipitate is separated off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-75b44e9437e64fdfadb1dfb22f743f7a
Source dataset
uspto-grants-1992_10
Patent number
US05155223

Reaction notes

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