Ethanol → 1-(1,2,2a,3,4,5-Hexahydroacenaphthylen-1-yl)piperidin-4-one

HRID 331226

반응식

HRID 331226 반응식
[CH:1]1([NH2:13])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1.C(=O)([O-])[O-].[K+].[K+].C(O)C.[I-].C([N+]1(C)[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]1)C>O>[CH:1]1([N:13]2[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1

참가 물질

6

반응물 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 110975681-Ethyl-1-methyl-4-oxopiperidin-1-ium iodideHCID 638213741,2,2a,3,4,5-Hexahydroacenaphthylen-1-amine

생성물 1

HCID 687066711-(1,2,2a,3,4,5-Hexahydroacenaphthylen-1-yl)piperidin-4-one수율 14%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

To a mixture of 1,2,2a,3,4,5-hexahydroacenaphthylen-1-ylamine, potassium carbonate (3.89 g) and ethanol (60 ml) was added 1-ethyl-1-methyl-4-oxopiperidinium iodide (8.36 g) dissolved in water (15 ml), and the mixture was heated under reflux for 2 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over magnesium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 1-(1,2,2a,3,4,5-hexahydroacenaphthylen-1-yl)piperidin-4-one (1.01 g, 14%) as an oil.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-27bbfc698e0847b9a4e7cddf3b391f15
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877779B2

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