Hydrochloride methanol → (E)-4-[2-(2-fluorophenyl)vinyl]piperidine

HRID 1837723Notes

Reaction equation

HRID 1837723 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[F:20])[CH2:8][CH2:7]1)=O)=C.Cl.CO>>[F:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1/[CH:13]=[CH:12]/[CH:9]1[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 226787831-(vinyloxycarbonyl)-4-[(E)-2-(2-fluorophenyl)-1-ethenyl]piperidine

Product 1

HCID 22248269(E)-4-[2-(2-fluorophenyl)vinyl]piperidineYield 97.9%

Procedure

904 mg of 1-(vinyloxycarbonyl)-4-[(E)-2-(2-fluorophenyl)-1-ethenyl]piperidine was suspended in 5 ml of a 10% hydrogen chloride-methanol solution. After stirring for 15 minutes at room temperature, the mixture was heated at 70° C. for one hour. The solvent was evaporated, and water and ethyl acetate were added to the residue, to separate the aqueous layer. The aqueous layer was basified with a diluted ammonia, and extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, to give 660 mg of the title compound as a colorless oil.

Workup

  1. temperaturethe mixture was heated at 70° C. for one hour
  2. customThe solvent was evaporated
  3. additionwater and ethyl acetate were added to the residue
  4. customto separate the aqueous layer
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b1437d05714c4e428c6059b7aab18ff2
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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