Isobutyl iodide → 1-Isobutylpiperidin-2-one

HRID 1810771ノート

反応式

HRID 1810771 の反応式
[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]

参加物

6

反応物 3

HCID 10556Isobutyl iodideHCID 126652-PiperidoneHCID 14797Potassium Hydroxide

生成物 1

HCID 190987571-Isobutylpiperidin-2-one収率 11.9%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3ebfe2dc8e7443f8958dc89b181f25fd
出典データセット
uspto-grants-2013_01
特許番号
US08362058B2

反応ノート

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