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

HRID 2042389Notes

Reaction equation

HRID 2042389 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. extractionsaturated NaCl solution (50 ml) and the product extracted with dichloromethane (2×100 ml)
  2. washThe organic layer was washed with water (2×100 ml)
  3. customdried
  4. customevaporated in vacuo
  5. customto give a white solid
  6. washColumn chromatography eluting with increasing proportions of ether in dichloromethane
  7. customgave pure DC-0009B (0.68 g, 80%) as a white powder

Sources & evidence

ORD record
ord-94c28992047d44039afca87bf5ef8fd4
Source dataset
uspto-grants-2013_11
Patent number
US08586585B2

Reaction notes

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