Potassium Carbonate → 2-Chloro-4-(4-ethylpiperazin-1-yl)benzaldehyde

HRID 577029Notes

Reaction equation

HRID 577029 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([N:16]2[CH2:17][CH2:18][N:13]([CH2:11][CH3:12])[CH2:14][CH2:15]2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 1450242-Chloro-4-fluorobenzaldehyde

Product 1

HCID 595894762-Chloro-4-(4-ethylpiperazin-1-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a 250 mL round bottom flask, 2-chloro-4-fluorobenzaldehyde (3.15 g, 20 mmol), 1-ethylpiperazine (2.8 mL, 22 mmol), and potassium carbonate (2.76 g, 20 mmol) were dissolved in anhydrous DMF (20 mL). The mixture was heated at 100° C. for 4 hours. DMF was evaporated under vacuum. The crude product was partitioned between water (100 mL) and DCM (150 mL). The organic phase was separated, washed with water, dried over Na2SO4, and evaporated to provide nearly pure 2-chloro-4-(4-ethylpiperazin-1-yl)benzaldehyde.

Workup

  1. customDMF was evaporated under vacuum
  2. customThe crude product was partitioned between water (100 mL) and DCM (150 mL)
  3. customThe organic phase was separated
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-eadbd9907a864eca99103244b62269a6
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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