Hydrochloric Acid → 2,6-Diethyl-2,3,6-trimethylpiperidin-4-one

HRID 2419165Notes

Reaction equation

HRID 2419165 reaction equation
[CH2:1]([C:3]1([CH3:14])N=[C:7]([CH2:9][CH3:10])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4]1)[CH3:2].Cl.C(=O)([O-])[O-:17].[K+].[K+]>[Br-].[NH4+].CO>[CH2:1]([C:3]1([CH3:14])[CH:9]([CH3:10])[C:7](=[O:17])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 11430Potassium CarbonateHCID 205278902,4,6-Triethyl-2,6-dimethyl-1,2,5,6-tetrahydropyrimidine

Product 1

HCID 221822132,6-Diethyl-2,3,6-trimethylpiperidin-4-one

Reagents, catalysts & solvents 2

HCID 25514Ammonium BromideCatalystHCID 887MethanolSolvent

Procedure

19.6 g of 2,4,6-triethyl-2,6-dimethyl-1,2,5,6-tetrahydropyrimidine and 0.4 g of ammonium bromide were added to 200 ml of methanol. To the mixture was added dropwise 10 g of 37% hydrochloric acid at 10° C., with stirring. After completion of the addition the whole was stirred at room temperature for 4 hours and there was then added a further 20 ml of 18% hydrochloric acid, The mixture was then heated at 30°-40° C for 7 hours and allowed to stand overnight at room temperature. The mixture was made alkaline with 40% aqueous potassium carbonate solution and, after methanol had been distilled off under reduced pressure, the mixture was extracted with ether. The ether solution was dried over potassium carbonate and the ether was removed. The residue was subjected to distillation under reduced pressure to give 15.1 g of 2,6-diethyl-2,3,6-trimethyl-4-oxopiperidine as an oil boiling at 91°-93° C/2.0 mm Hg.

Workup

  1. additionAfter completion of the addition the whole
  2. stirringwas stirred at room temperature for 4 hours
  3. temperatureThe mixture was then heated at 30°-40° C for 7 hours
  4. distillationafter methanol had been distilled off under reduced pressure
  5. extractionthe mixture was extracted with ether
  6. dry with materialThe ether solution was dried over potassium carbonate
  7. customthe ether was removed
  8. distillationThe residue was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-f0975d14bc6c4157a9d55cdae8ec820a
Source dataset
uspto-grants-1978_08
Patent number
US04105626

Reaction notes

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