Reaktion #10279

Reaktionsgleichung

aminoacetaldehyde dimethylacetal

5-chlorovaleryl chloride

sodium hydride

→

1-(2,2-dimethoxyethyl)-piperidin-2-one

Ausbeute 80.9%

Lösungsmittel

ethyl acetate

sodium carbonate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe aqueous layer was separated
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe combined organic phase was washed with 1% hydrochloric acid and water
4. 4
   Trocknendried (magnesium sulfate)
5. 5
   Einengenconcentrated
6. 6
   workup.DISSOLUTIONThe oily residue was dissolved in tetrahydrofuran
7. 7
   TemperaturThe reaction mixture was heated
8. 8
   Temperaturunder reflux for 1.5 hours
9. 9
   Filtrationfiltered
10. 10
    EinengenThe filtrate was concentrated

Vorschrift

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.

Quelle