Water → 3-Azidopiperidin-2-one

HRID 34135Notes

Reaction equation

HRID 34135 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][C:3]1=[O:8].[N-:9]=[N+:10]=[N-:11].[Na+].O>CN(C)C=O>[N:9]([CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][C:3]1=[O:8])=[N+:10]=[N-:11]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 1181713-Bromopiperidin-2-one

Product 1

HCID 230701363-Azidopiperidin-2-oneYield 56.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2.0 g of 3-bromopiperidin-2-one in 30 ml of N,N-dimethylformamide was added 5.9 g of sodium azide, followed by stirring at 60° C. overnight. After cooling down to room temperature, water was added to the reaction mixture and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give 890 mg of the title compound as a yellow oil.

Workup

  1. temperatureAfter cooling down to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4b22bc59313e4936ae5b7c24eb6c20e4
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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