Water → 3,5-Diethyl-3-methyl-1-(phenylmethyl)-4-piperidinone

HRID 396310Notes

Reaction equation

HRID 396310 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10]([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C(I)C.O.[O:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:13][CH:25]([CH2:24][CH3:23])[C:26](=[O:22])[C:10]([CH2:11][CH3:12])([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6340IodoethaneHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 5609651-Benzyl-3-methyl-4-piperidone

Product 1

HCID 222788783,5-Diethyl-3-methyl-1-(phenylmethyl)-4-piperidinone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-Benzyl-3-methyl-piperidin-4-one (50 g, 246 mmole) was added to the stirred suspension of sodium hydride (12.0 g, 300.0 mmole) in tetrahydrofuran (500 ml) at ambient temperature and stirring was continued for 1 hr. Ethyl iodide (42.5 ml, 520.0 mmole) in dry tetrahydrofuran (100 ml) was added it at 0-5° C. The resulting mixture stirred at room temperature for 18 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 5% ethyl acetate in hexane afforded 1-benzyl-3,5-diethyl-3-methylpiperidin-4-one. Yield 12.0 g (19%), C17H25NO, m/z 260 (M+1).

Workup

  1. stirringThe resulting mixture stirred at room temperature for 18 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 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-cd8fac6196d04a7a999cf56a9f06cb86
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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