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7-(4-Benzyl-3-methyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid → 1-Cyclopropyl-7-(3-methyl-1-piperazinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 2351916
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2351916
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]([CH3:24])=[C:22]3[C:17]([C:18](=[O:31])[C:19]([C:28]([OH:30])=[O:29])=[CH:20][N:21]3[CH:25]3[CH2:27][CH2:26]3)=[CH:16][C:15]=2[F:32])[CH2:10][CH:9]1[CH3:33])C1C=CC=CC=1>[Pd].C(O)(=O)C>[CH3:33][CH:9]1[NH:8][CH2:13][CH2:12][N:11]([C:14]2[C:23]([CH3:24])=[C:22]3[C:17]([C:18](=[O:31])[C:19]([C:28]([OH:30])=[O:29])=[CH:20][N:21]3[CH:25]3[CH2:26][CH2:27]3)=[CH:16][C:15]=2[F:32])[CH2:10]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 156224977-(4-Benzyl-3-methyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Produkt 1

HCID 140525871-Cyclopropyl-7-(3-methyl-1-piperazinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acidAusbeute 66,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To 7-(4-benzyl-3-methyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.30 g) are added acetic acid (10 ml) and 10% Pd-C (50 mg), and the mixture is subjected to catalytic reduction at 70° C. under atmospheric pressure for one hour. After the catalytic reduction, the reaction mixture is cooled and the catalyst is removed by filtration. The filtrate is concentrated, and to the residue is added water, and the mixture is adjusted to about pH 7.5 with sodium hydrogen carbonate, and then is extracted with dichloromethane. The dichloromethane is distilled off, and to the residue is added diethyl ether, and the resulting precipitates are separated by filtration and recrystallized from ethanol to give 7-(3-methyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.16 g), as pale yellow powder, m.p. 206°-208° C.

Aufarbeitung

  1. temperatureAfter the catalytic reduction, the reaction mixture is cooled
  2. customthe catalyst is removed by filtration
  3. concentrationThe filtrate is concentrated
  4. additionto the residue is added water
  5. extractionis extracted with dichloromethane
  6. distillationThe dichloromethane is distilled off
  7. additionto the residue is added diethyl ether
  8. customthe resulting precipitates
  9. customare separated by filtration
  10. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-4d258fda736645ea9621bab83044e595
Quelldatensatz
uspto-grants-1989_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04874764

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