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

HRID 331226

Reaction equation

HRID 331226 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-27bbfc698e0847b9a4e7cddf3b391f15
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Linked notes

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