Piperazine → 3-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-

HRID 373520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 373520
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6][N:7]2[CH:14]1[CH2:16][CH2:15]1.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6][N:7]2[CH:14]1[CH2:16][CH2:15]1

Komponenten

4

Edukt 2

HCID 4837PiperazineHCID 148802095-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Produkt 1

HCID 30788553-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-Ausbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 0.42 g of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 0.39 g of anhydrous piperazine and 10 ml of pyridine was heated under reflux for 2.5 hours. The reaction mixture was concentrated to dryness under reduced pressure, and the residue was washed with ethanol and then dissolved in water and a 1N aqueous solution of sodium hydroxide. The solution was neutralized with a 10% aqueous solution of acetic acid. The crystals which precipitated were collected by filtration, washed with water, and dried to give 0.44 g of 5-amino-1-cyclopropyl-6-fluoro-7-(1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid as pale yellow needles. m.p. 214°-216° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  4. washthe residue was washed with ethanol
  5. dissolutiondissolved in water
  6. customThe crystals which precipitated
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-795ba1a3d9da4a1ab1cbc3408ac73340
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05164392

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