Water → 1-Benzyl-3,5-dimethyl-3-ethyl-4-piperidone

HRID 396335Notes

Reaction equation

HRID 396335 reaction equation
[CH2:1]([N:8]1[CH2:13]C[C:11](=O)[CH:10](CC)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:19]I.O.[O:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:9][CH:10]([CH3:11])[C:26](=[O:22])[C:25]([CH3:19])([CH2:24][CH3:23])[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6328Methyl iodideHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 64909601-Benzyl-3-ethylpiperidin-4-one

Product 1

HCID 222788971-Benzyl-3,5-dimethyl-3-ethyl-4-piperidone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-Benzyl-3-ethyl-piperidin-4-one (33 g, 152.0 mmole) was added to the stirred suspension of sodium hydride (9.5 g, 200.0 mmole) in tetrahydrofuran (300 ml) at 32° C. and stirring was continued for 1 hr. Methyl iodide (30 ml, 490.0 mmole) in dry tetrahydrofuran (100 ml) was added it at 0-5° C. The resulting mixture stirred at room temperature for 4 hr, water (100 ml) and ethyl acetate (800 ml) were added respectively. Organic layer was separated, dried (Na2SO4) and concentrated to give crude product, which was purified through column chromatography. Elute from 10% ethyl acetate in hexane afforded 1-benzyl-3,5-dimethyl-3-ethylpiperidin-4-one. Yield 22.0 g (59%), C16H23NO, m/z 246 (M+1).

Workup

  1. stirringThe resulting mixture stirred at room temperature for 4 hr
  2. customOrganic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give crude product, which
  6. customwas purified through column chromatography
  7. washElute from 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-fa84d4909e204876ada75d2f233342d8
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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