Potassium Carbonate → 4-{[4-(Propan-2-yl)piperazin-1-yl]methyl}benzaldehyde

HRID 591788Notes

Reaction equation

HRID 591788 reaction equation
BrC[CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].[CH:18]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)([CH3:20])[CH3:19]>CN(C=O)C>[CH:18]([N:21]1[CH2:26][CH2:25][N:24]([CH2:3][C:4]2[CH:5]=[CH:6][C:7]([CH:8]=[O:9])=[CH:10][CH:11]=2)[CH2:23][CH2:22]1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 780131-IsopropylpiperazineHCID 110851354-(2-Bromoethyl)benzaldehyde

Product 1

HCID 866620354-{[4-(Propan-2-yl)piperazin-1-yl]methyl}benzaldehydeYield 97.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-(bromoethyl)benzaldehyde (0.200 g, 1.0 mmol) and K2CO3 (0.277 g, 2.0 mmol) in DMF (5 mL) was added N-isopropylpiperazine (0.129 g, 1.0 mmol) and the reaction was stirred at room temperature for 5 hours, then concentrated in vacuo. The resulting mixture was diluted with H2O and extracted with EtOAc. The organics were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford 4-((4-Isopropylpiperazin-1-yl)methyl)benzaldehyde (0.240 g, 97%).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe resulting mixture was diluted with H2O
  3. extractionextracted with EtOAc
  4. washThe organics were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a63aa1d34ef64ad8b344a3908eb1c517
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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