Sodium Carbonate → 1-(1-(2-Pyrazinyl)-ethyl)-4-oxopiperidine

HRID 2294937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2294937
[NH2:1][CH:2]([C:4]1[CH:9]=[N:8][CH:7]=[CH:6][N:5]=1)[CH3:3].C([O-])([O-])=O.[K+].[K+].[I-].C[N+]1(C)[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]1.C([O-])([O-])=O.[Na+].[Na+]>O.C(O)C>[N:5]1[CH:6]=[CH:7][N:8]=[CH:9][C:4]=1[CH:2]([N:1]1[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]1)[CH3:3]

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 111494971,1-Dimethyl-4-oxopiperidin-1-ium iodideHCID 185190061-(Pyrazin-2-yl)ethanamine

Produkt 1

HCID 214716861-(1-(2-Pyrazinyl)-ethyl)-4-oxopiperidineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred mixture of 2-(1-aminoethyl)pyrazine (225 mg), ethanol (10 mL) and K2CO3 (72 mg) heated to reflux was added dropwise over 30 min, a solution of 4 g of 1,1-dimethyl-4-oxopiperidinium iodide (2.1 g) in water (36 mL). When the addition was complete, the mixture was heated under reflux for an additional 2 h, cooled, basified to pH 10 with Na2CO3 and extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure. Column chromatography over silica gel, eluting with a gradient of ethyl acetate; 0-5% methanol gave 300 mg of 1-(1-(2-pyrazinyl)-ethyl)-4-oxopiperidine as an oil: 1H NMR (400 MHz, CDCl3) 8.74 (d, 1H), 8.54 (dd, 1H), 8.48 (d, 1H), 3.94 (q, 1H), 2.89-2.75 (m, 4H), 2.46 (t, 4H), 1.50 (d, 3H).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux
  3. additionwas added dropwise over 30 min
  4. additionWhen the addition
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for an additional 2 h
  7. temperaturecooled
  8. extractionextracted with ethyl acetate (3×100 mL)
  9. dry with materialThe combined organic extracts were dried over MgSO4
  10. concentrationconcentrated under reduced pressure
  11. washColumn chromatography over silica gel, eluting with a gradient of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e6934d0c12a046e4a982734c3e545b57
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05691323

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