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

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.

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

ORD record

ord-22ef774146e94e6399813806a464e1d3

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361648B2