Piperazine → Piperazine, 1,4-bis(1,3-benzodioxol-5-ylmethyl)-

HRID 2358489Notes

Reaction equation

HRID 2358489 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:9]1[O:19][C:18]2[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][C:11]=2[O:10]1.[OH-:20].[Na+]>CN(C=O)C>[CH2:9]1[O:19][C:18]2[CH:17]=[CH:16][C:13]([CH2:14][N:1]3[CH2:6][CH2:5][N:4]([CH2:14][C:13]4[CH:16]=[CH:17][C:18]5[O:20][CH2:9][O:10][C:11]=5[CH:12]=4)[CH2:3][CH2:2]3)=[CH:12][C:11]=2[O:10]1

Participants

6

Reactant 4

HCID 4837PiperazineHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 887131,3-Benzodioxole, 5-(chloromethyl)-

Product 1

HCID 96702Piperazine, 1,4-bis(1,3-benzodioxol-5-ylmethyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of piperazine (207 mg) in dry DMF (5 ml) under nitrogen was added sodium hydride (80% w/w in oil, 250 mg), followed by 3,4-methylenedioxybenzylchloride (0.90 g) and the mixture stirred at room temperature overnight Aqueous NaOH (50 ml, 1M) was added slowly, then saturated NaCl solution (50 ml) and the product extracted with dichloromethane (2×100 ml). The organic layer was washed with water (2×100 ml), dried and evaporated in vacuo to give a white solid. Column chromatography eluting with increasing proportions of ether in dichloromethane gave pure DC-0009B (0.68 g, 80%) as a white powder.

Workup

  1. additionwas added slowly
  2. extractionsaturated NaCl solution (50 ml) and the product extracted with dichloromethane (2×100 ml)
  3. washThe organic layer was washed with water (2×100 ml)
  4. customdried
  5. customevaporated in vacuo
  6. customto give a white solid
  7. washColumn chromatography eluting with increasing proportions of ether in dichloromethane
  8. customgave pure DC-0009B (0.68 g, 80%) as a white powder

Sources & evidence

ORD record
ord-ecb94fc8e4a747c7aa9a009bd58d1d2e
Source dataset
uspto-grants-2010_07
Patent number
US07763747B2

Reaction notes

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