Ethanol → 1-(1-(5-Pyrimidinyl)-ethyl)-4-oxopiperidine

HRID 2294928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2294928
[NH2:1][CH:2]([C:4]1[CH:5]=[N:6][CH:7]=[N:8][CH:9]=1)[CH3:3].C(O)C.C([O-])([O-])=O.[K+].[K+].[I-].C[N+]1(C)[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1>O>[N:6]1[CH:5]=[C:4]([CH:2]([N:1]2[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]2)[CH3:3])[CH:9]=[N:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 11430Potassium Carbonate2×HCID 111494971,1-Dimethyl-4-oxopiperidin-1-ium iodideHCID 189142881-(Pyrimidin-5-yl)ethanamine

Produkt 1

HCID 189142901-(1-(5-Pyrimidinyl)-ethyl)-4-oxopiperidineAusbeute 26,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred mixture of 1.1 g of 5-(1-aminoethyl)pyrimidine (O. Cervinska and P. Malon, Coll. Czechoslov. Chem. Commun. 1977, 42, 3464-72.), 17 mL of ethanol and 1.36 g of K2CO3 heated to reflux was added dropwise over 30 min, a solution of 4 g of 1,1-dimethyl-4 -oxopiperidinium iodide in 70 mL of water. When the addition was complete, the mixture was heated under reflux for an additional 2 h, cooled, basified to pH 9 with K2CO3 and extracted with 5 times with 50 mL portions of methylene chloride. The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure. Chromatography over silica gel, eluting with 90:10 CH3CN:MeOH gave 0.48 g of 1-(1-(5-pyrimidinyl)-ethyl)-4-oxopiperidine as an oil: 1H NMR (400 MHz, CDCl3) 9.14 (s, 1H), 8.78 (s, 2H), 3.8 (q, J=7 Hz, 1H), 2.7-2.9 (m, 4H), 2.45 (m, 4H), 1.5 (d, J=7 Hz, 3H).

Aufarbeitung

  1. temperatureto reflux
  2. additionwas added dropwise over 30 min
  3. additionWhen the addition
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for an additional 2 h
  6. temperaturecooled
  7. extractionextracted with 5 times with 50 mL portions of methylene chloride
  8. dry with materialThe combined organic extracts were dried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. washChromatography over silica gel, eluting with 90:10 CH3CN

Quellen und Nachweise

ORD-Eintrag
ord-9728a89e3ab6476283f28af2817b3473
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05691323

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