Methyl iodide → 1-Benzyl-3-methyl-4-piperidone

Participants

Reaction Steps

To a suspension (160 ml) of 3.2 g of sodium hydride in tetrahydrofuran (THF) was added a solution (15 ml) of 15.0 g of 1-benzyl-4-piperidone in THF in an ice bath, and the solution was stirred at room temperature for 30 minutes. 5.92 ml of methyl iodide was added to this solution, and the solution was stirred at 60° C. for 4 hours. The salt precipitated was separated by filtration, and after concentrating the filtrate under reduced pressure, water was added to the concentrate. The solution was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and from the fractions eluted with ethyl acetate-hexane (1:1 v/v) was obtained 3.98 g of 1-benzyl-3-methyl-4-piperidone (yield: 25%).

Provenance & Evidence