Methyl iodide → 1-Benzyl-3,5-dimethylpiperidin-4-one

Temperature

-78 °C

To 1-benzyl-3-methyl-4-piperidone (2.0 g, 9.8 mmol) in THF at about −78° C. under argon, was added Lithium diisopropylamide (7.35 ml, 14.7 mmol, 2 M in heptane/THF/ethylbenzene). After stirring for about 1 hour at about −78° C., iodomethane (0.73 ml, 11.8 mmol) was added. The reaction mixture was stirred for about 1 hour at about −78° C., then warmed to room temperature. Stirring was continued overnight at room temperature. The reaction was quenched with saturated ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with water, then brine and dried over magnesium sulfate. The crude product was chromatographed on silica gel, eluting with EtOAc/hexane (3:10) to give a yellow oil of the title compound.

1. stirringThe reaction mixture was stirred for about 1 hour at about −78° C.
2. temperaturewarmed to room temperature
3. stirringStirring
4. waitwas continued overnight at room temperature
5. customThe reaction was quenched with saturated ammonium chloride solution
6. extractionextracted with ethyl acetate
7. washThe organic layer was washed with water
8. dry with materialbrine and dried over magnesium sulfate
9. customThe crude product was chromatographed on silica gel
10. washeluting with EtOAc/hexane (3:10)

ORD record

ord-7e930039295a48bba18c56d8066747b6

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07541365B2