Sodium Carbonate → 4-(2-Methoxyethyl)piperazine-1-carbaldehyde

HRID 1740380Notes

Reaction equation

HRID 1740380 reaction equation
[CH:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)=[O:2].C(=O)([O-])[O-].[Na+].[Na+].[CH3:15][O:16][CH2:17][CH2:18]Br>CO>[CH:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:18][CH2:17][O:16][CH3:15])[CH2:5][CH2:4]1)=[O:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 809722-Bromoethyl methyl etherHCID 821911-Piperazinecarboxaldehyde

Product 1

HCID 218386494-(2-Methoxyethyl)piperazine-1-carbaldehydeYield 102.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 37.1 g of N-formylpiperazine and 37.1 g of anhydrous sodium carbonate in 50 mL of methanol was added dropwise 53.15 g of methoxyethyl bromide, and the mixture was refluxed for 3.5 hours. After cooling to room temperature, insolubles were filtered out and the filtrate was concentrated. To the residue was added water and chloroform. After separating the organic layer, the aqueous layer was extracted with chloroform. The combined organic layer was dried over anhydrous magnesium sulfate and concentrated to give 57.2 g of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 3.5 hours
  2. filtrationinsolubles were filtered out
  3. concentrationthe filtrate was concentrated
  4. additionTo the residue was added water and chloroform
  5. customAfter separating the organic layer
  6. extractionthe aqueous layer was extracted with chloroform
  7. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-aaaf1bfb69a940fe969a8ee59137fee5
Source dataset
uspto-grants-1999_10
Patent number
US05969138

Reaction notes

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