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

HRID 481774Notes

Reaction equation

HRID 481774 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:17]I>O1CCCC1>[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH:12]([CH3:17])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 192201-Benzyl-4-piperidoneHCID 24758Sodium hydride

Product 1

HCID 5609651-Benzyl-3-methyl-4-piperidoneYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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%).

Workup

  1. stirringthe solution was stirred at 60° C. for 4 hours
  2. customThe salt precipitated
  3. customwas separated by filtration
  4. concentrationafter concentrating the filtrate under reduced pressure, water
  5. additionwas added to the concentrate
  6. extractionThe solution was extracted with ethyl acetate
  7. washthe organic layer was washed with saturated aqueous solution of sodium chloride
  8. dry with materialdried with anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography
  11. washfrom the fractions eluted with ethyl acetate-hexane (1:1 v/v)

Sources & evidence

ORD record
ord-ece9cb0e2dde473882be5661d36f1738
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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