Piperazine → HCID 18675000, compound

HRID 1634869Notes

Reaction equation

HRID 1634869 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[CH2:15][Cl:16])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.[C:27](=[O:30])([O-])[O-].[K+].[K+]>CN(C=O)C>[ClH:16].[ClH:16].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[CH2:15][N:21]2[CH2:26][CH2:25][N:24]([CH2:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:30][CH3:27])[CH:6]=3)[CH2:23][CH2:22]2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 120163292-(3,4,5-Trimethoxyphenyl)benzyl chloride

Product 1

HCID 18675000HCID 18675000, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-(3,4,5-Trimethoxyphenyl)benzyl chloride (298 mg) and piperazine (43 mg) were dissolved in DMF (5 mL), and to the solution potassium carbonate (138 mg) was added. The mixture was stirred at 80° C. for 4 hours and concentrated under reduced pressure. Water was added to the residue to conduct extraction with chloroform. The resultant organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=40:1) to obtain a free base of the title compound. This compound was dissolved in ethyl acetate, and to the solution an ethyl acetate solution of 4 M hydrogen chloride was added to provide a dihydrochloride.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionextraction with chloroform
  4. washThe resultant organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-bb5e5ef0ae3141f789427982c2b9505e
Source dataset
uspto-grants-2003_01
Patent number
US06509329B1

Reaction notes

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