Acetic Acid → HCID 58826597, compound

To a suspension of (S)-3-(2-methoxyethyl)piperidine hydrochloride (46.70 g, 260 mmol), sodium acetate (46.90 g, 572 mmol) and acetic acid (33.1 ml, 572 mmol) in tetrahydrofuran (470 ml) was added dropwise chloroacetyl chloride (28.3 ml, 7.53 mmol) under ice-cooling, and the mixture was stirred overnight at temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give (S)-3-(2-methoxyethyl)-N-(chloroacetyl)piperidine (45.0 g, yield 78.8%).

1. temperaturecooling
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationAfter filtration
6. customthe solvent was evaporated under reduced pressure
7. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

ORD record

ord-027793a9ec3c43b59678431b079a2a69

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977331B1