Dimethylformamide → 1-Benzyl-2-piperidone

HRID 259752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 259752
[H-].[Na+].[C:3]1(=[O:9])[NH:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CN(C)C=O>C1(C)C=CC=CC=1>[CH2:10]([N:8]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 126652-PiperidoneHCID 24758Sodium hydride

Produkt 1

HCID 51700761-Benzyl-2-piperidoneAusbeute 42,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel3×

Versuchsvorschrift

To a suspension of sodium hydride (80%, 3.3 g, 0.11 mol) in dry toluene (250 ml) under argon, was added dropwise a solution of δ-valerolactam (9.9 g, 0.10 mol) in toluene (50 ml). When the addition was complete, the mixture was heated under reflux for 1 h, then cooled to ambient temperature. A solution of benzyl bromide (13 ml, 18.8 g, 0.11 mol) in toluene (50 ml) containing dimethyl formamide (1 ml) was then added dropwise over 15 minutes. The resulting mixture was heated under reflux for 4 h. On cooling, the mixture was filtered and the filtrate was dried (Na2SO4) and evaporated in vacuo to give an oil. Bulb-to-bulb distillation gave the title compound (D26) as a yellow oil (8.0 g).

Aufarbeitung

  1. additionWhen the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 h
  4. additionwas then added dropwise over 15 minutes
  5. temperatureThe resulting mixture was heated
  6. temperatureunder reflux for 4 h
  7. temperatureOn cooling
  8. filtrationthe mixture was filtered
  9. dry with materialthe filtrate was dried (Na2SO4)
  10. customevaporated in vacuo
  11. customto give an oil
  12. distillationBulb-to-bulb distillation

Quellen und Nachweise

ORD-Eintrag
ord-46712f5af6e442ae81975eac26efe3ca
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05523299

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