Ammonia → 2,2,6,6-Tetramethyl-3-(prop-2-en-1-yl)piperidin-4-one

HRID 616541Notes

Reaction equation

HRID 616541 reaction equation
[CH2:1]([CH:4]1[C:9]([CH3:11])([CH3:10])[NH:8][C:7]([CH3:13])([CH3:12])[CH:6]=[C:5]1N1CCCCC1)[CH:2]=[CH2:3].C([O-])(=[O:22])C.[Na+].C(=O)(O)[O-].[Na+].N>C(O)(=O)C.O>[CH2:1]([CH:4]1[C:5](=[O:22])[CH2:6][C:7]([CH3:13])([CH3:12])[NH:8][C:9]1([CH3:11])[CH3:10])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 213303855-Allyl-1,2,5,6-tetrahydro-2,2,6,6-tetramethyl-4-piperidinopyridine

Product 1

HCID 213304902,2,6,6-Tetramethyl-3-(prop-2-en-1-yl)piperidin-4-oneYield 83.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1.46 g of the 5-allyl-1,2,5,6-tetrahydro-2,2,6,6-tetramethyl-4-piperidinopyridine thus obtained were dissolved in a mixture of 3 ml of acetic acid, 1.5 g of sodium acetate and 3 ml of water, and the solution was allowed to stand overnight. To the solution were then added 6.0 g of sodium bicarbonate and 3 ml of concentrated aqueous ammonia; the mixture was then extracted with hexane. The extract was dried over anhydrous magnesium sulphate and then treated with charcoal. 0.91 g of the title compound was obtained after removal of the hexane. The compound showed a single spot on thin layer chromatography using a 0.25 mm thick layer of alumina and a mixture of benzene/hexane/ethyl acetate/triethylamine (2 : 2 : 1: 0.5 by volume) as developing solvent; Rf value 0.70.

Workup

  1. extractionthe mixture was then extracted with hexane
  2. dry with materialThe extract was dried over anhydrous magnesium sulphate
  3. additiontreated with charcoal

Sources & evidence

ORD record
ord-9c00ef3baf0143bc8bb34f8827d70c61
Source dataset
uspto-grants-1978_02
Patent number
US04075165

Reaction notes

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