Potassium Carbonate → HCID 18536291, compound

HRID 412058Notes

Reaction equation

HRID 412058 reaction equation
Cl[C:2]1[N:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[N:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1.C1OCCOCCOCCOCCOCCOC1>CN(C=O)C>[N:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:25][CH2:26][N:27]([C:2]3[N:11]=[CH:10][CH:9]=[CH:8][C:3]=3[C:4]([O:6][CH3:7])=[O:5])[CH2:28][CH2:29]2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 705171-(4-Pyridyl)piperazineHCID 819931Methyl 2-chloronicotinate

Product 1

HCID 18536291HCID 18536291, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.4 g of methyl chloronicotinate, 5.5 g of potassium carbonate, 3.3 g of 4-pyridylpiperazine and a spatula tipful of 18-crown-6 were heated at 100° C. for 5 h in 75 ml of DMF and then stirred at room temperature for 60 h. The excess potassium carbonate was filtered off, the filtrate was concentrated and the residue was partitioned between water and ethyl acetate. After drying the organic phase over magnesium sulfate and concentrating the solvent, 3.9 g (82%) of the product were obtained.

Workup

  1. filtrationThe excess potassium carbonate was filtered off
  2. concentrationthe filtrate was concentrated
  3. customthe residue was partitioned between water and ethyl acetate
  4. dry with materialAfter drying the organic phase over magnesium sulfate
  5. concentrationconcentrating the solvent

Sources & evidence

ORD record
ord-5303cd42f8b647349761e54dab303ad8
Source dataset
uspto-grants-2003_05
Patent number
US06562827B1

Reaction notes

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