Piperazine → HCID 12733906, compound

HRID 544238Notes

Reaction equation

HRID 544238 reaction equation
[OH: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].[OH: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 12733881HCID 12733881, compound

Product 1

HCID 12733906HCID 12733906, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-(2-hydroxyethyl)-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 2.85 g (0.01 mole), piperazine 4.3 g (0.05 mole) and pyridine 4 ml was refluxed at 135°-145° C. for 8 hours by heating. After cooling, the reaction mixture was evaporated under vacuum. The residue was acidified with acetic acid and the insoluble matters were removed by filtration. The filtrate was neutralized with an aqueous solution of caustic soda. The precipitated crystals were collected by filtration, washed with water and dried. The crystals were dissolved in hot diluted hydrochloric acid, ethanol was added and the solution was cooled to precipitate crystals. The precipitated crystals were collected by filtration, washed with ethanol, dried, and recrystallized from ethanol to obtain 1.9 g (51%) of 1-(2-hydroxyethyl)-6-fluoro-7-(1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride. Colorless powders.

Workup

  1. temperaturewas refluxed at 135°-145° C. for 8 hours
  2. temperatureby heating
  3. temperatureAfter cooling
  4. customthe reaction mixture was evaporated under vacuum
  5. customthe insoluble matters were removed by filtration
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with water
  8. customdried
  9. dissolutionThe crystals were dissolved in hot diluted hydrochloric acid
  10. additionethanol was added
  11. temperaturethe solution was cooled
  12. customto precipitate crystals
  13. filtrationThe precipitated crystals were collected by filtration
  14. washwashed with ethanol
  15. customdried
  16. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3013fbb7311846bda4428f5eac6fba13
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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