Sodium Hydroxide → 2,2,6,6-Tetramethyl-4-piperidone

HRID 1077003Notes

Reaction equation

HRID 1077003 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.O.C1(C)C=CC(S(O)(=O)=[O:20])=CC=1.[OH-].[Na+]>CN(C)C=O>[CH3:10][C:4]1([CH3:11])[NH:5][C:6]([CH3:9])([CH3:8])[CH2:7][C:2](=[O:20])[CH2:1]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 68396Pyrimidine, 1,2,5,6-tetrahydro-2,2,4,6,6-pentamethyl-HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 132202,2,6,6-Tetramethyl-4-piperidoneYield 88.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 15.4 g. of acetonine in 100 ml. of dimethylformamide was added with 19.0 g. of p-toluenesulfonic acid monohydrate. The mixture was stirred at room temperature for 8 hours, then allowed to stand overnight to complete the reaction. After completion of the reaction, the reaction mixture was added with 30% aqueous sodium hydroxide solution and extracted with ether. The extract was dried over anhydrous potassium carbonate and ether was distilled off. The resulting residue was purified by distillation under reduced pressure to obtain triacetonamine in a yield of 88.8%.

Workup

  1. waitto stand overnight
  2. customthe reaction
  3. customAfter completion of the reaction
  4. extractionextracted with ether
  5. dry with materialThe extract was dried over anhydrous potassium carbonate and ether
  6. distillationwas distilled off
  7. distillationThe resulting residue was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-1afa5fe61472441ab07593bbd6c884af
Source dataset
uspto-grants-1976_05
Patent number
US03959298

Reaction notes

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