Diethyl Ether → 4-Acetylpiperidin-2-one

HRID 535313Notes

Reaction equation

HRID 535313 reaction equation
CON(C)[C:4]([CH:6]1[CH2:11][CH2:10][NH:9][C:8](=[O:12])[CH2:7]1)=[O:5].C[Mg+].[Br-].[CH3:17]COCC>C1COCC1>[C:4]([CH:6]1[CH2:11][CH2:10][NH:9][C:8](=[O:12])[CH2:7]1)(=[O:5])[CH3:17]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 86718437N-methoxy-N-methyl-2-oxopiperidine-4-carboxamideHCID 178418689HCID 178418689, compound

Product 1

HCID 571689834-Acetylpiperidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-methoxy-N-methyl-2-oxopiperidine-4-carboxamide (2.72 g, 9.79 mmol) in THF (30 ml) was immersed in an ice-bath. MeMgBr (3M) in Et2O (4.57 ml, 13.70 mmol) was added slowly and the remaining white suspension was stirred for 1 h in an ice-bath and over night at room temperature. The reaction mixture was quenched carefully with aqueous saturated NaHCO3 and extracted with DCM. The organic layers were washed with brine, combined, dried over Na2SO4, filtered and concentrated in vacuo to obtain the title compound as yellow-brown oil. The crude product was directly used in the next step.

Workup

  1. customThe reaction mixture was quenched carefully with aqueous saturated NaHCO3
  2. extractionextracted with DCM
  3. washThe organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3896b49d54cc4dc2b9c435c680afe2c3
Source dataset
uspto-grants-2014_10
Patent number
US08859535B2

Reaction notes

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