Ethyl Acetate → HCID 58550238, compound

HRID 2068875Notes

Reaction equation

HRID 2068875 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:7].[H-].[Na+].Br[CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].C(OCC)(=O)C>CN(C)C=O.O>[O:7]=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][N:1]1[CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 126652-PiperidoneHCID 24758Sodium hydrideHCID 62576Benzyl bromoacetate

Product 1

HCID 58550238HCID 58550238, compoundYield 24.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, to a solution of piperidin-2-one (9.8 g, 99 mmol) in N,N-dimethylformamide (100 ml) was added sodium hydride (4.4 g, 110 mmol) under ice-cooling, and the mixture was stirred for 1 hr. Then, benzyl bromoacetate (19 ml, 120 mmol) was added, and the mixture was further stirred for 2 hr. To the reaction mixture were added ethyl acetate and water, and the organic layer was separated, washed successively with water and saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound (6.0 g, yield 24%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 2 hr
  3. customthe organic layer was separated
  4. washwashed successively with water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. customSodium sulfate was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-14ef7ff3cd4f4eb6aa30df3a9c5290b8
Source dataset
uspto-grants-2012_10
Patent number
US08299070B2

Reaction notes

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