Sodium Carbonate → 1-[(5-Chloro-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-4-[(E)-2-(2-fluorophenyl)-1-ethenyl]piperidine

HRID 1837772Notes

Reaction equation

HRID 1837772 reaction equation
[Cl:1][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]=3[F:25])[CH2:13][CH2:12]2)[C:5]([O:8]C)=[N:6][CH:7]=1.C(OCC)(=O)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][N:11]2[CH2:12][CH2:13][CH:14](/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[CH2:15][CH2:16]2)[C:5](=[O:8])[NH:6][CH:7]=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 98411871-[(5-Chloro-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-4-[(E)-2-(2-fluorophenyl)-1-ethenyl]piperidineYield 49.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (8 ml) was dissolved 245 mg of 1-[(5-chloro-2-methoxy-3-pyridinyl)methyl]-4-[(E)-2-(2-fluorophenyl)-1-ethenyl]piperidine. To the mixture was added 7 ml of a 4N-hydrogen chloride-ethyl acetate solution, followed by heating under reflux for 7 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 resulting oil to be crystallized, and 116 mg of the title compound was obtained as a slight yellow powder.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 7 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 resulting oil
  7. customto be crystallized

Sources & evidence

ORD record
ord-f33110541bac4ce6a685c00e71523ced
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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