Water → 1-[5-(4-Methoxy-benzenesulfonyl)2-methoxy-phenyl]piperazine

HRID 2416668Notes

Reaction equation

HRID 2416668 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][C:4]=1[N:13]1[CH2:18][CH2:17][N:16](C(=O)C(F)(F)F)[CH2:15][CH2:14]1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([Mg]Br)=[CH:29][CH:28]=1.[OH-].[Na+].O>C1COCC1>[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([N:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[CH:5]=2)(=[O:10])=[O:11])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 121366554-Methoxy-3-[4-(2,2,2-trifluoro-acetyl)-piperazin-1-yl]-benzenesulfonyl chlorideHCID 178491912HCID 178491912, compound

Product 1

HCID 99689601-[5-(4-Methoxy-benzenesulfonyl)2-methoxy-phenyl]piperazineYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-methoxy-3-[4-(2,2,2-trifluoro-acetyl)-piperazin-1-yl]-benzenesulfonyl chloride (0.19 g), prepared as in Example 1 Step 2, in THF (0.5 ml) at 0° C. under argon atmosphere was added dropwise a solution of 4-methoxyphenylmagnesium bromide in THF (0.5M, 2 ml; 1 mmol). After stirring at this temperature for 1 h. A solution of 6N NaOH (0.5 ml) was added and the reaction mixture was stirred at ambient temperature for 20 h. Water was added (10 ml) and the mixture was extracted into ethyl acetate (20 ml). The organic phase was dried (Na2SO4) and concentrated in vacuo to give 1-[5-(4-methoxy-benzenesulfonyl)2-methoxy-phenyl]piperazine as a white solid (0.65 g, 36%), MS, MH+ 363.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 20 h
  2. extractionthe mixture was extracted into ethyl acetate (20 ml)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-749f4815bc714a1d877f34835426b867
Source dataset
uspto-grants-2004_11
Patent number
US06825202B2

Reaction notes

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