Piperazine → 1-[[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]-methyl]piperazine

HRID 1267621Notes

Reaction equation

HRID 1267621 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)[CH:4]=1.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:20][O:19][C:11]1[CH:10]=[C:9]([C:5]2[CH:4]=[C:3]([CH2:2][N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[CH:8]=[CH:7][N:6]=2)[CH:14]=[C:13]([O:15][CH3:16])[C:12]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 120192374-Chloromethyl-2-(3,4,5-trimethoxyphenyl) pyridine

Product 1

HCID 120211551-[[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]-methyl]piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloromethyl-2-(3,4,5-trimethoxyphenyl)pyridine (13.52 g) and piperazine (11.89 g) were dissolved in DMF (100 mL), and to the solution potassium carbonate (15.89 g) was added. The mixture was stirred at room temperature for 5 hours. After the reaction mixture was concentrated under reduced pressure, chloroform was added to the residue, and the mixture was washed with water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=20:1 to chloroform:ammonia-saturated methanol=10:1) to obtain a free base of the title compound.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure, chloroform
  2. additionwas added to the residue
  3. washthe mixture was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=20:1 to chloroform:ammonia-saturated methanol=10:1)

Sources & evidence

ORD record
ord-3e04258af26d4f4f8ad50ab562893996
Source dataset
uspto-grants-2003_04
Patent number
US06552188B2

Reaction notes

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