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Piperazine → 6-Fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-5-methyl-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid

HRID 1081432
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1081432
[F:1][C:2]1[C:3]([CH3:27])=[C:4]2[C:9](=[CH:10][C:11]=1F)[N:8]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[F:20])[CH:7]=[C:6]([C:21]([O:23]CC)=[O:22])[C:5]2=[O:26].[NH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>C(#N)C>[F:1][C:2]1[C:3]([CH3:27])=[C:4]2[C:9](=[CH:10][C:11]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[N:8]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[F:20])[CH:7]=[C:6]([C:21]([OH:23])=[O:22])[C:5]2=[O:26]
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Komponenten

4

Edukt 2

HCID 4837PiperazineHCID 14774107Ethyl 1-(2,4-difluorophenyl)-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Produkt 1

HCID 146512396-Fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-5-methyl-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acidAusbeute 69,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 0.76 g (2.00 mmol) of ethyl 6,7-difluoro-1-(2,4-difluorophenyl)-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylate, 0.69 g (8.00 mmol) of anhydrous piperazine, and 30 mL of acetonitrile was refluxed for 18 hours, cooled, and concentrated. The residue was dissolved in 20 mL 6N hydrochloric acid and refluxed for 3 hours. The suspension was cooled, concentrated by half and filtered, and the solids were washed with water. The crude product was suspended in water which was made basic (pH 12), and the resulting solution was filtered and neutralized to pH 6.8. The precipitate which formed was filtered, washed with water, and dried to give 0.58 g of the title compound, mp 198°-200° C.

Aufarbeitung

  1. temperaturecooled
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in 20 mL 6N hydrochloric acid
  4. temperaturerefluxed for 3 hours
  5. temperatureThe suspension was cooled
  6. concentrationconcentrated by half
  7. filtrationfiltered
  8. washthe solids were washed with water
  9. filtrationthe resulting solution was filtered
  10. customThe precipitate which formed
  11. filtrationwas filtered
  12. washwashed with water
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-52bf604a28f44bbe815f6dd4ca564c0e
Quelldatensatz
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05585491

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