Sodium hydride → 1-(2,2-Dimethoxyethyl)-piperidin-2-one

HRID 10183

Reaktionsgleichung

Reaktionsgleichung von HRID 10183
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].Cl[CH2:9][CH2:10][CH2:11][CH2:12][C:13](Cl)=[O:14].[H-].[Na+]>C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][N:5]1[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1=[O:14]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 740895-Chlorovaleryl chlorideHCID 89728Aminoacetaldehyde dimethyl acetal

Produkt 1

HCID 219785091-(2,2-Dimethoxyethyl)-piperidin-2-oneAusbeute 80,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

To a stirred mixture of aminoacetaldehyde dimethylacetal (0.74 g, 7 mmole) in ethyl acetate (20 mL) and 2M sodium carbonate (20 mL) was added 5-chlorovaleryl chloride (1.55 g, 10 mmole). The reaction mixture was stirred at ambient temperature for 1 hour. The aqueous layer was separated and extracted with ethyl acetate. The combined organic phase was washed with 1% hydrochloric acid and water, dried (magnesium sulfate), and concentrated. The oily residue was dissolved in tetrahydrofuran, and sodium hydride (60% in oil) (0.3 g, 7.5 mmole) was added. The reaction mixture was heated under reflux for 1.5 hours and filtered. The filtrate was concentrated to give 1-(2,2-dimethoxyethyl)-piperidin-2-one (1.06 g) as a pale yellow oil.

Aufarbeitung

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phase was washed with 1% hydrochloric acid and water
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. dissolutionThe oily residue was dissolved in tetrahydrofuran
  7. temperatureThe reaction mixture was heated
  8. temperatureunder reflux for 1.5 hours
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-1a741121a16944648d852fb3d307e1e8
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094778B2

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