Piperazine → HCID 12733904, compound

HRID 544219Notes

Reaction equation

HRID 544219 reaction equation
[F:1][CH2:2][CH2:3][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.[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>N1C=CC=CC=1>[ClH:14].[F:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:15])=[C:11]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:12]=2)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 127338801-(2-Fluoroethyl)-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 12733904HCID 12733904, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-(2-fluoroethyl)-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (0.87 g) (3 millimole), piperazine (1.3 g) (15 millimole) and pyridine (4 ml) piperazine was heated at 135° to 145° C. for 12 hours. After cooling, the reaction mixture was evaporated under vacuum, the residue was acidified with acetic acid, the undissolved matter was filtered off. The filtrate was neutralized in an aqueous solution of caustic soda. The precipitate was filtered, washed, dried and dissolved in diluted HCl. Ethanol was added and the solution was ice cooled. The precipitate was filtered, washed with ethanol and dried and recrystallized from ethanol to obtain 0.30 g (27%) of 1-(2-fluoroethyl)-6-fluoro-7-(1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride in powder form.

Workup

  1. temperaturewas heated at 135° to 145° C. for 12 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated under vacuum
  4. filtrationthe undissolved matter was filtered off
  5. filtrationThe precipitate was filtered
  6. washwashed
  7. customdried
  8. dissolutiondissolved in diluted HCl
  9. additionEthanol was added
  10. temperaturecooled
  11. filtrationThe precipitate was filtered
  12. washwashed with ethanol
  13. customdried
  14. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8b333a19b7424aac81f98f6775d506ab
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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