Methyl Ethyl Ketone → 2,6-Diethyl-2,3,6-trimethylpiperidin-4-one

HRID 616534Notes

Reaction equation

HRID 616534 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].C(C(C)=[O:18])C.O.O.[Cl-].[Ca+2].[Cl-].[OH-].[Na+]>O>[CH2:1]([C:3]1([CH3:14])[CH:9]([CH3:10])[C:7](=[O:18])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 14798Sodium HydroxideHCID 6093260Calcium chloride, dihydrateHCID 205278902,4,6-Triethyl-2,6-dimethyl-1,2,5,6-tetrahydropyrimidine

Product 1

HCID 221822132,6-Diethyl-2,3,6-trimethylpiperidin-4-oneYield 82.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To an ice-cooled mixture of 39.2 g of 2,4,6-triethyl-2,6-dimethyl-1,2,5,6-tetrahydropyrimidine and 18.0 g of methyl ethyl ketone were added 14.7 g of powdered calcium chloride dihydrate, followed by 3 ml of water. The resulting mixture was heated at 60° C, with stirring, for 15 hours, made alkaline by the addition of a 35% aqueous solution of sodium hydroxide and extracted with diethyl ether. The etheral solution was then dried over potassium carbonate and the diethyl ether was evaporated off. The residue was distilled under reduced pressure, giving 32.4 g of the title compound. Boiling point 91° - 93° C/2.0 mmHg.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe etheral solution was then dried over potassium carbonate
  3. customthe diethyl ether was evaporated off
  4. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-c545f235b5f9443eb40f3c98da8c03ff
Source dataset
uspto-grants-1978_02
Patent number
US04075165

Reaction notes

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