Methyl iodide → 1-Benzyl-3,3-dimethylpiperidin-4-one

HRID 556943Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 556943
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16]C(C)([O-])C.[K+].CI>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C:10]([CH3:16])([CH3:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 5609651-Benzyl-3-methyl-4-piperidoneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 97944131-Benzyl-3,3-dimethylpiperidin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-Benzyl-3-methyl-piperidin-4-one (2.03 g, 10 mmol) in THF (10 mL) was added potassium t-Butoxide (1.1 g, 10 mmol) and methyl iodide (0.62 mL, 10 mmol). The solution was then stirred at room temperature for about 72 hours. The reaction was quenched with brine and extracted with ethyl acetate. The combined organic layers were concentrated in vacuo, then purified by flash chromatography on silica gel (35 g SiO2, gradient elution from 100% hexane to 100% ethyl acetate) to yield the title compound as a colorless oil.

Aufarbeitung

  1. customThe reaction was quenched with brine
  2. extractionextracted with ethyl acetate
  3. concentrationThe combined organic layers were concentrated in vacuo
  4. custompurified by flash chromatography on silica gel (35 g SiO2, gradient elution from 100% hexane to 100% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-054dde9eeaf1466ea4c1481de9e9e565
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058287B2

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