Methyl iodide → 1-(4-Bromophenyl)-4-methylpiperazine

HRID 646478Notes

Reaction equation

HRID 646478 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:14](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27356291-(4-Bromophenyl)piperazine

Product 1

HCID 118176751-(4-Bromophenyl)-4-methylpiperazineYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(4-Bromo-phenyl)-piperazine (19, 4.1 mmol) and potassium carbonate (1.89, 3 eq) in DMF (15 ml) treated with methyl iodide (250 μl, 1.1 equivalents), solution stirred at room temperature overnight. Reaction quenched with deionised water (10 ml), extracted with ethyl acetate. Organic phase washed with sodium hydrogen carbonate to remove any dimethylated impurity, dried and solvent removed to give 1-(4-Bromo-phenyl)-4-methyl-piperazine in 73% yield.

Workup

  1. customReaction
  2. customquenched with deionised water (10 ml)
  3. extractionextracted with ethyl acetate
  4. washOrganic phase washed with sodium hydrogen carbonate
  5. customto remove any dimethylated impurity
  6. customdried
  7. customsolvent removed

Sources & evidence

ORD record
ord-cfc74b61ba60429ead76b4dafd2a0f67
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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