Methanol → HCID 67442149, compound

HRID 1667317Notes

Reaction equation

HRID 1667317 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11](/[CH:14]=[CH:15]/[C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:23])[CH:10]([CH3:24])[CH2:9]1)C1C=CC=CC=1.[Cl:25]C(OC(Cl)C)=O.CO>ClCCCl>[ClH:25].[CH3:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([CH3:22])[C:16]=1/[CH:15]=[CH:14]/[CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]1[CH3:24]

Participants

5

Reactant 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 67442667HCID 67442667, compound

Product 1

HCID 67442149HCID 67442149, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 125 mg of 1-benzyl-4-[(E)-2-(2,6-dimethylphenyl)vinyl]-3-methylpiperidine in 3 ml of 1,2-dichloroethane, 139 mg of 1-chloroethyl chloroformate was added at ambient temperature. The mixture was heated under reflux for 1 hour. After cooling, 10 ml of methanol was added to the reaction mixture and the resulting mixture was heated under reflux for further 30 minutes. After cooling, the solvent was evaporated under reduced pressure. The residue was dissolved in 5 ml of ethyl acetate and the solution was filtered. To the filtrate was added 1 ml of 4N hydrochloric acid-ethyl acetate and the solvent was evaporated under reduced pressure. The residue was triturated in ethyl acetate. After filtration, the obtained solid was recrystallized from ethyl acetate-methanol to give 47 mg of 4-[(E)-2-(2,6-dimethylphenyl)vinyl]-3-methylpiperidine hydrochloride.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. temperaturethe resulting mixture was heated
  5. temperatureunder reflux for further 30 minutes
  6. temperatureAfter cooling
  7. customthe solvent was evaporated under reduced pressure
  8. dissolutionThe residue was dissolved in 5 ml of ethyl acetate
  9. filtrationthe solution was filtered
  10. additionTo the filtrate was added 1 ml of 4N hydrochloric acid-ethyl acetate
  11. customthe solvent was evaporated under reduced pressure
  12. customThe residue was triturated in ethyl acetate
  13. filtrationAfter filtration
  14. customthe obtained solid was recrystallized from ethyl acetate-methanol

Sources & evidence

ORD record
ord-448fe0328c3d4bc2a18379f4483b8448
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

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