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Ethyl Acetate → (E)-3-[4-[2-(2-Fluorophenyl)vinyl]piperidino]methyl-1H-pyrazin-2-one

HRID 890091
Notes
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Reaction equation

HRID 890091 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[C:18]([O:23]C)=[N:19][CH:20]=[CH:21][N:22]=2)[CH2:12][CH2:11]1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(O)C.S(Cl)(Cl)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[CH:10]1[CH2:11][CH2:12][N:13]([CH2:16][C:17]2[C:18](=[O:23])[NH:19][CH:20]=[CH:21][N:22]=2)[CH2:14][CH2:15]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 22248227(E)-3-[4-[2-(2-Fluorophenyl)vinyl]piperidino]methyl-2-methoxypyrazine

Product 1

HCID 22247936(E)-3-[4-[2-(2-Fluorophenyl)vinyl]piperidino]methyl-1H-pyrazin-2-oneYield 63.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 24386
Thionyl Chloride
Solvent

Procedure

After dissolving 296 mg of (E)-3-[4-[2-(2-fluorophenyl)vinyl]piperidino]methyl-2-methoxypyrazine in 5 ml of ethanol, 1 ml of thionyl chloride was added and the mixture was heated to reflux for 9 hours. Aqueous sodium carbonate solution was added to the reaction solution and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue and the mixture was filtered to obtain the title compound (180 mg, 63% yield).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 9 hours
  4. washThe organic layer was washed with water and saturated brine in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionEthyl acetate was added to the residue
  8. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-a0ccaa95e8ba448eb81b1e7b523605a8
Source dataset
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06995144B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes