Water → HCID 59204917, compound

HRID 2241903Notes

Reaction equation

HRID 2241903 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:14][CH2:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][C:25]=2[F:33])[CH2:20][CH2:19]1)=[O:17].O>CN(C)C=O>[F:33][C:25]1[CH:26]=[C:27]([N+:30]([O-:32])=[O:31])[CH:28]=[CH:29][C:24]=1[N:21]1[CH2:20][CH2:19][N:18]([C:16](=[O:17])[CH2:15][CH2:14][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 59204963HCID 59204963, compound

Product 1

HCID 59204917HCID 59204917, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Piperidine (0.081 g, 0.950 mmol) and potassium carbonate (0.380 g, 2.77 mmol) were added to a solution of 3-chlor-1-[4-(2-fluoro-4-nitrophenyl)piperazin-1-yl]propan-1-one (compound of Reference Example 58; 0.250 g, 0.790 mmol) in anhydrous N,N-dimethylformamide (6 ml), and the mixture was stirred at room temperature for 10 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:2) to give the title compound (0.120 g, 41%) as a yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained by evaporation of the solvent under reduced pressure
  5. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-185634b09ebd45c789125ecf23fc3ac1
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

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