Potassium Carbonate → 4-(3,5-Dimethylpiperazin-1-yl)benzaldehyde

HRID 591642Notes

Reaction equation

HRID 591642 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][CH:11]1[CH2:16][NH:15][CH2:14][CH:13]([CH3:17])[NH:12]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:10][CH:11]1[NH:12][CH:13]([CH3:17])[CH2:14][N:15]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:16]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 660562,6-DimethylpiperazineHCID 680234-Fluorobenzaldehyde

Product 1

HCID 866620204-(3,5-Dimethylpiperazin-1-yl)benzaldehydeYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-fluorobenzaldehyde (2.0 g, 16.1 mmol), 2,6-dimethylpiperazine (2.2 g, 19.3 mmol), and K2CO3 (2.7 g, 19.3 mmol) in DMF (10 mL) was heated at 120° C. for 4 hours. Then, the reaction was diluted with H2O and extracted with EtOAc. The organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel eluting with 3% to 10% MeOH/CH2Cl2 afforded 4-(3,5-dimethylpiperazin-1-yl)benzaldehyde (2.0 g, 57%).

Workup

  1. extractionextracted with EtOAc
  2. washThe organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel eluting with 3% to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-c26f7d226a024a26a95b314d497a86d9
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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