Sodium Carbonate → 1-[(2-Oxo-1,2-dihydro-3-pyridinyl)methyl]-4-[(E)-2-[(2-cyclohexylmethyloxy)phenyl]-1-ethenyl]piperidine Oxalate

HRID 1837773Notes

Reaction equation

HRID 1837773 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH2:10][N:11]2[CH2:16][CH2:15][CH:14](/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3F)[CH2:13][CH2:12]2)[C:5]([O:8]C)=[N:6][CH:7]=1.[C:26]([O:29][CH2:30][CH3:31])(=[O:28])C.Cl.[C:33](=[O:36])([O-:35])[O-].[Na+].[Na+]>C(O)C>[C:26]([OH:29])(=[O:28])[C:33]([OH:35])=[O:36].[O:8]=[C:5]1[C:4]([CH2:10][N:11]2[CH2:16][CH2:15][CH:14](/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:36][CH2:33][CH:31]3[CH2:30][CH2:4][CH2:3][CH2:2][CH2:7]3)[CH2:13][CH2:12]2)=[CH:3][CH:2]=[CH:7][NH:6]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 226785031-[(5-Chloro-2-methoxy-3-pyridinyl)methyl]-4-[(E)-2-(2-fluorophenyl)-1-ethenyl]piperidine

Product 1

HCID 865902981-[(2-Oxo-1,2-dihydro-3-pyridinyl)methyl]-4-[(E)-2-[(2-cyclohexylmethyloxy)phenyl]-1-ethenyl]piperidine Oxalate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (12 ml) was dissolved 221 mg of 1-[(5-chloro-2-methoxy-3-pyridinyl)methyl]-4-[(E)-2-(2-fluorophenyl)-1-ethenyl]piperidine. To the mixture was added 12 ml of a 4N-hydrogen chloride-ethyl acetate solution, followed by heating under reflux for 11 hours. An aqueous sodium carbonate was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then the solvent was evaporated. Ether was added to the obtained oil, to crystallize. The title compound (176 mg) was obtained as a light pink powder.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 11 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. additionEther was added to the obtained oil
  7. customto crystallize

Sources & evidence

ORD record
ord-16ee16cd200e4314af7d476588b87bdb
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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