3,4-Dichlorobenzyl chloride → HCID 64844081, compound

HRID 496208Notes

Reaction equation

HRID 496208 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][C:3]=1[Cl:10].[CH3:11][CH:12]1[CH2:17][NH:16][CH:15]([CH3:18])[CH2:14][NH:13]1.CCOC(C)=O.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[Cl:10][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:2]=1[Cl:1])[CH2:8][N:13]1[CH2:14][CH:15]([CH3:18])[NH:16][CH2:17][CH:12]1[CH3:11]

Participants

6

Reactant 4

HCID 76093,4-Dichlorobenzyl chlorideHCID 78162,5-DimethylpiperazineHCID 8857Ethyl AcetateHCID 10340Sodium Carbonate

Product 1

HCID 64844081HCID 64844081, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1,2-dichloro-4-chloromethyl-benzene (1.1 ml 7.89 mmol) in DMF (5 ml) was added to 2,5-dimethyl-piperazine (1.0 g, 8.77 mmol) dissolved in DMF (25 ml). The reaction was stirred over night, poured into a mixture of EtOAc and sodium carbonate (5%). The water phase was washed twice with EtOAc and the combined organic phase once with brine, and dried over sodium sulfate. After evaporation the crude was dissolved in methanol. The dibensylated piperazine does not dissolve. The filtrate was filtered through a short silica column, using methanol as eluant and evaporated to give the pure product. Yield 812 mg, 38%

Workup

  1. washThe water phase was washed twice with EtOAc
  2. dry with materialthe combined organic phase once with brine, and dried over sodium sulfate
  3. customAfter evaporation the crude
  4. dissolutionwas dissolved in methanol
  5. dissolutionThe dibensylated piperazine does not dissolve
  6. filtrationThe filtrate was filtered through a short silica column
  7. customevaporated
  8. customto give the pure product

Sources & evidence

ORD record
ord-79da541319fe431da9e9ce7c5e25a5f6
Source dataset
uspto-grants-2005_09
Patent number
US06943188B2

Reaction notes

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