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2-Methylpiperazine → Ethyl 1-ethyl-8-(3-methyl-1-piperazinyl)-4H-quinolizin-4-one-3-carboxylate

HRID 1851
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1851
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([CH:11]=1)=[C:9]([CH2:12][CH3:13])[CH:8]=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6]2=[O:19].[CH3:20][CH:21]1[CH2:26][NH:25][CH2:24][CH2:23][NH:22]1>N1C=CC=CC=1>[CH2:12]([C:9]1[CH:8]=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6](=[O:19])[N:5]2[C:10]=1[CH:11]=[C:2]([N:25]1[CH2:24][CH2:23][NH:22][CH:21]([CH3:20])[CH2:26]1)[CH:3]=[CH:4]2)[CH3:13]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 660572-MethylpiperazineHCID 10660349Ethyl 8-chloro-1-ethyl-4-oxo-4H-quinolizine-3-carboxylate

Produkt 1

HCID 19691415Ethyl 1-ethyl-8-(3-methyl-1-piperazinyl)-4H-quinolizin-4-one-3-carboxylateAusbeute 100,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Ethyl 8-chloro-1-ethyl-4H-quinolizin-4-one-3-carboxylate (558 mg, 2.0 mmol), the product of Step 3 of Example 62, was dissolved in 10 mL of dry pyridine under a nitrogen atmosphere. To the resultant solution was added 600 mg (6.0 mmol) of 2-methylpiperazine and the stirred reaction mixture was heated at 65° C. for 3 hours. The reaction mixture was allowed to cool to ambient temperature and then concentrated in vacuo in order to remove all of the pyridine. The residue was dissolved in 60 mL of methylene chloride and the methylene chloride solution was washed with 60 mL of water. The aqueous layer was extracted with 2 X 60 mL of methylene chloride and the combined methylene chloride solutions were dried over anhydrous sodium sulfate, filtered and concentrated and dried in vacuo to afford 690 mg of the title compound. The product was carried on to the next step without purification.

Aufarbeitung

  1. customthe stirred reaction mixture
  2. temperatureto cool to ambient temperature
  3. concentrationconcentrated in vacuo in order
  4. customto remove all of the pyridine
  5. dissolutionThe residue was dissolved in 60 mL of methylene chloride
  6. washthe methylene chloride solution was washed with 60 mL of water
  7. extractionThe aqueous layer was extracted with 2 X 60 mL of methylene chloride
  8. dry with materialthe combined methylene chloride solutions were dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dbb3e314646f42c4828e49ee8c678c63
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05726182

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