Sodium Iodide → 3-Methyl-4-(3-trifluoromethoxy-phenyl)-piperazin-2-one

HRID 1096251Notes

Reaction equation

HRID 1096251 reaction equation
[I-].[Na+].C([O-])(O)=O.[Na+].Cl[CH:9]([CH3:27])[C:10]([NH:12][CH2:13][CH2:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=1)=[O:11]>CC(C)=O>[CH3:27][CH:9]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=2)[CH2:14][CH2:13][NH:12][C:10]1=[O:11]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 667831992-Chloro-N-[2-(3-trifluoromethoxy-phenylamino)-ethyl]-propionamide

Product 1

HCID 667830063-Methyl-4-(3-trifluoromethoxy-phenyl)-piperazin-2-oneYield 66.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium iodide (64 mg, 0.43 mmol) and NaHCO3 (86 mg, 1.03 mmol) were added to a solution of 2-chloro-N-[2-(3-trifluoromethoxy-phenylamino)-ethyl]-propionamide (266 mg, 0.86 mmol) in acetone (20 mL). The reaction mixture was heated at reflux for 72 h, then evaporated. The residue was partitioned between EtOAc and water. The organic layer was dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane/EtOAc gradient) afforded the title compound (156 mg, 66%). Yellow oil, MS: 275.1 (M+H)−.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 72 h
  3. customevaporated
  4. customThe residue was partitioned between EtOAc and water
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-66d3ae7731f04706afc3609aa0c226d2
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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