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

Temperature

60 °C

At first, 4.2 g of 60% sodium hydride was suspended in 200 ml of tetrahydrofuran, and then a solution of 18.9 g of 1-benzyl-4-piperidone and 17.9 g of methyl iodide dissolved in 20 ml of tetrahydrofuran was added dropwise to the suspension at room temperature over 5 minutes. Thereafter, the mixture was heated to 60° C. and stirred for 5 hours. Thereafter, the reaction mixture was filtered. The filtrate was concentrated, and then the concentrate was poured into 150 ml of water and extracted with 120 ml portions of ethyl acetate three times. The extract was washed with 150 ml of brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 21.6 g of an oily matter. The oily matter was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=2:1 V/V) to obtain 8.0 g of 1-benzyl-3-methyl-4-piperidone.

1. additionwas added dropwise to the suspension at room temperature over 5 minutes
2. filtrationThereafter, the reaction mixture was filtered
3. concentrationThe filtrate was concentrated
4. additionthe concentrate was poured into 150 ml of water
5. extractionextracted with 120 ml portions of ethyl acetate three times
6. washThe extract was washed with 150 ml of brine
7. dry with materialdried over anhydrous sodium sulfate
8. distillationThe solvent was distilled off under reduced pressure
9. customto obtain 21.6 g of an oily matter
10. customThe oily matter was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=2:1 V/V)

ORD record

ord-e6ee90eb5bee4a0b9be8c8a2ce183781

Source dataset

uspto-grants-1987_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04639522