Hydrochloride methanol → HCID 22248046, compound

HRID 1837722Notes

Reaction equation

HRID 1837722 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][CH:9](/[CH:12]=[CH:13]/[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:8][CH2:7]1)=O)=C.Cl.CO>>[CH:22]1([CH2:21][O:20][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2/[CH:13]=[CH:12]/[CH:9]2[CH2:10][CH2:11][NH:6][CH2:7][CH2:8]2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 22678472HCID 22678472, compound

Product 1

HCID 22248046HCID 22248046, compoundYield 94.8%

Procedure

2.026 g of 1-(vinyloxycarbonyl)-4-[(E)-2-[(2-cyclohexylmethyloxy)phenyl]-1-ethenyl]piperidine was suspended in 20 ml of a 10% hydrogen chloride-methanol solution, and the mixture was stirred for 20 minutes under ice-cooling. After stirring for 15 minutes at room temperature, the mixture was heated under reflux for one hour 10 minutes. The solvent was evaporated, and to the residue was added an aqueous saturated sodium bicarbonate. The mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and to the residue was added n-heptane. The insoluble matters were filtered off, and the filtrate was evaporated, to give 1.556 g of the title compound as a colorless oil.

Workup

  1. temperaturecooling
  2. stirringAfter stirring for 15 minutes at room temperature
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for one hour 10 minutes
  5. customThe solvent was evaporated
  6. additionto the residue was added an aqueous saturated sodium bicarbonate
  7. extractionThe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with water and brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated
  11. additionto the residue was added n-heptane
  12. filtrationThe insoluble matters were filtered off
  13. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-4388fb3062484b52a75338a47e90b974
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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