1-Methylpiperazine → 5-((4-Methylpiperazine-1-yl)methyl)furan-2-carboxaldehyde

HRID 336836

Reaction equation

HRID 336836 reaction equation
Br[CH2:2][C:3]1[O:7][C:6]([CH:8]=[O:9])=[CH:5][CH:4]=1.[CH3:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>O1CCOCC1>[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([CH2:2][C:3]2[O:7][C:6]([CH:8]=[O:9])=[CH:5][CH:4]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 119704915-(Bromomethyl)-2-furaldehyde

Product 1

HCID 866713815-((4-Methylpiperazine-1-yl)methyl)furan-2-carboxaldehydeYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.20 g (1.1 mmol) of 5-(bromomethyl)furan-2-carboxaldehyde in anhydrous dioxane (10 ml) are added 261 μL (0.24 g, 2.3 mmol) of 1-methylpiperazine. The mixture is stirred at room temperature for 30 min. The precipitate formed is filtered and rinsed with dioxane. The filtrate is concentrated, dissolved in dichloromethane, and washed in water. The organic phase is dried over magnesium sulfate, filtered, and concentrated. The residue obtained is purified by chromatography on silica (eluent: 7N NH4OH in MeOH/CH2Cl2, 5:95) to yield 0.12 g (55%) of 5-((4-methylpiperazine-1-yl)methyl)furan-2-carboxaldehyde in the form of an orange solid.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered
  3. washrinsed with dioxane
  4. concentrationThe filtrate is concentrated
  5. dissolutiondissolved in dichloromethane
  6. washwashed in water
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue obtained
  11. customis purified by chromatography on silica (eluent: 7N NH4OH in MeOH/CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-c4556eb69876429c80231218238a6038
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Linked notes

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