Isobutyl iodide → 1-Isobutylpiperidin-2-one

HRID 402262Notes

Reaction equation

HRID 402262 reaction equation
[OH-].[K+].[NH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9].I[CH2:11][CH:12]([CH3:14])[CH3:13]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:11]([N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9])[CH:12]([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 10556Isobutyl iodideHCID 126652-PiperidoneHCID 14797Potassium Hydroxide

Product 1

HCID 190987571-Isobutylpiperidin-2-oneYield 11.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent2×

Procedure

A suspension of 85% potassium hydroxide (36.6 g), and tetrabutylammonium bromide (9.1 g) in toluene (400 ml) was refluxed overnight in a Dean Stalk apparatus. Then, a solution of 2-piperidone (50.0 g) and iodoisobutane (120.7 g) in toluene (150 ml) was added dropwise at 115° C. to the solution above. After the dropwise addition, the mixture was refluxed further for 2.5 hours, and then cooled, and filtered to remove insoluble matter. The filtrate was washed with water, and the aqueous layer was extracted with toluene. The organic layers were combined and dried over magnesium sulfate. After distilling off the solvent under reduced, the residue was separated and purified by silica gel column chromatography (ethyl acetate) to obtain yellow oil of 1-isobutyl-2-piperidone (9.3 g).

Workup

  1. temperaturewas refluxed overnight in a Dean Stalk apparatus
  2. additionAfter the dropwise addition
  3. temperaturethe mixture was refluxed further for 2.5 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. customto remove insoluble matter
  7. washThe filtrate was washed with water
  8. extractionthe aqueous layer was extracted with toluene
  9. dry with materialdried over magnesium sulfate
  10. distillationAfter distilling off the solvent
  11. customthe residue was separated
  12. custompurified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-ef64e2d41b1c4fe08c486c9956d40855
Source dataset
uspto-grants-2014_06
Patent number
US08741943B2

Reaction notes

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