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

HRID 2097264Notes

Reaction equation

HRID 2097264 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-e2e00e6193614a38bfc5fc41ea13a8da
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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