Piperazine → HCID 70495429, compound

HRID 544232Notes

Reaction equation

HRID 544232 reaction equation
[CH2:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:15])=[C:11]([Cl:14])[CH:12]=2)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]1)[CH:2]=[CH2:3].[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>N1C=CC=CC=1>[ClH:14].[CH2:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:15])=[CH:11][CH:12]=2)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[C:5]1[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 12733883HCID 12733883, compound

Product 1

HCID 70495429HCID 70495429, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-allyl-6-fluoro-7-chloro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 0.94 g, piperazine 2.9 g and 2 ml of pyridine was refluxed for 8 hours by heating. After cooling, the reaction mixture was evaporated under vacuum. The residue was dissolved in an aqueous solution of acetic acid and the insoluble matters were removed by filtration. The filtrate was neutralized with an aqueous solution of NaOH. The precipitated crystals were collected by filtration, washed with water and dried. Recrystallizing the crystals from a mixed solvent of concentrated hydrochloric acid and ethanol, 0.32 g (26%) of 1-allyl-6-fluoro-1,4-dihydro-4-oxo-(1-piperazinyl)-quinoline-3-carboxylic acid hydrochloride was obtained. Colorless powders.

Workup

  1. temperaturewas refluxed for 8 hours
  2. temperatureby heating
  3. temperatureAfter cooling
  4. customthe reaction mixture was evaporated under vacuum
  5. dissolutionThe residue was dissolved in an aqueous solution of acetic acid
  6. customthe insoluble matters were removed by filtration
  7. filtrationThe precipitated crystals were collected by filtration
  8. washwashed with water
  9. customdried
  10. customRecrystallizing the crystals from a mixed solvent of concentrated hydrochloric acid and ethanol

Sources & evidence

ORD record
ord-7600cdb8ef0d4da8b970c72fb0d66730
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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