Nitric Acid → 2,2,6,6-Tetramethyl-4-piperidone

HRID 1077002Notes

Reaction equation

HRID 1077002 reaction equation
[CH3:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[NH:5][C:4]([CH3:11])([CH3:10])N=1.[N+]([O-])(O)=[O:13]>CO.CC(C)=O.O>[CH3:10][C:4]1([CH3:11])[NH:5][C:6]([CH3:9])([CH3:8])[CH2:7][C:2](=[O:13])[CH2:1]1

Participants

6

Reactant 2

HCID 944Nitric AcidHCID 68396Pyrimidine, 1,2,5,6-tetrahydro-2,2,4,6,6-pentamethyl-

Product 1

HCID 132202,2,6,6-Tetramethyl-4-piperidoneYield 119%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

5.0 g. of Acetonine was dissolved in a mixed solvent comprising 10 g. of acetone and 10 g. of methanol. The solution was added dropwise with a solution of 2.1 g. of nitric acid containing 0.63 g. of water in 10 g. of acetone and 10 g. of methanol at 15°-20°C. After completion of the addition, the mixture was maintained at room temperature for 24 hours to effect the reaction. After completion of the reaction, the reaction mixture was purified in the same manner as in Example 5 to obtain triacetonamine in a yield of 119%.

Workup

  1. additionThe solution was added dropwise with a solution of 2.1 g
  2. customat 15°-20°C
  3. additionAfter completion of the addition
  4. customthe reaction
  5. customAfter completion of the reaction
  6. customthe reaction mixture was purified in the same manner as in Example 5

Sources & evidence

ORD record
ord-e1ed4fe389e34ff6a1151522544895c2
Source dataset
uspto-grants-1976_05
Patent number
US03959298

Reaction notes

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