Isobutyl iodide → 1-Isobutylpiperidin-2-one

HRID 402262노트

반응식

HRID 402262 반응식
[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]

참가 물질

6

반응물 3

HCID 10556Isobutyl iodideHCID 126652-PiperidoneHCID 14797Potassium Hydroxide

생성물 1

HCID 190987571-Isobutylpiperidin-2-one수율 11.9%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ef64e2d41b1c4fe08c486c9956d40855
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741943B2

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