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

HRID 1891148Notes

Reaction equation

HRID 1891148 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 (1 g, 4.1 mmol) and potassium carbonate (1.8 g, 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-4d4b75024b6341e8ac0e2dc885ab75f2
Source dataset
uspto-grants-2013_08
Patent number
US08507480B2

Reaction notes

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