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

HRID 630070Notes

Reaction equation

HRID 630070 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-dbe4e4dc4bec4cee978d8dd60da6191a
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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