Sodium Carbonate → trans-3,7-dimethylhexahydro-1H-azepine-2-one

HRID 14578Notes

Reaction equation

HRID 14578 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([CH3:8])[C:3]1=[N:9]O.C(=O)([O-])[O-:12].[Na+].[Na+]>C1(C)C(C)=CC=CC=1>[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([CH3:8])[NH:9][C:3]1=[O:12]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 40531046trans-2,6-Dimethylcyclohexanone oxime

Product 1

HCID 66594919trans-3,7-dimethylhexahydro-1H-azepine-2-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Into 20 ml of xylene were added 1.3 g of trans-2,6-dimethylcyclohexanone oxime and 6 g of polyphosphoric acid, the mixture was stirred for 10 hours at 100%. The reaction mixture was cooled to near room temperature, poured into ice-water. Sodium carbonate was added to the mixture, and the mixture was extracted with ethyl acetate three times. The organic layers was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 1.2 g of trans-3,7-dimethylhexahydro-1H-azepine-2-one.

Workup

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. washThe organic layers was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7aec735a879148f49e91979006a0a2c6
Source dataset
uspto-grants-2010_06
Patent number
US07732448B2

Reaction notes

Loading…