Urea → Glutarimide, 2,2-dimethyl-

HRID 14579

Reaction equation

HRID 14579 reaction equation
[CH3:1][C:2]([CH3:11])([CH2:6][CH2:7][C:8](O)=[O:9])[C:3](O)=[O:4].[NH2:12]C(N)=O>O>[CH3:1][C:2]1([CH3:11])[CH2:6][CH2:7][C:8](=[O:9])[NH:12][C:3]1=[O:4]

Participants

4

Reactant 2

HCID 1176UreaHCID 126812,2-Dimethylglutaric acid

Product 1

HCID 121048Glutarimide, 2,2-dimethyl-Yield 86.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

The mixture of 10 g of 2,2-dimethylglutaric acid and 37.5 g of urea was stirred for 8 hours at 160° C. Into the reaction mixture was added water at 100° C., and the mixture was cooled to near room temperature. The mixture was extracted with ethyl acetate three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 7.6 g of 3,3-dimethylpiperidin-2,6-dione.

Workup

  1. temperaturethe mixture was cooled to near room temperature
  2. extractionThe mixture was extracted with ethyl acetate three times
  3. washThe organic layers were washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-839758e16358461ea01e3ad93e9d6318
Source dataset
uspto-grants-2010_06
Patent number
US07732448B2

Linked notes

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