Potassium Carbonate → HCID 59168283, compound

HRID 2195066Notes

Reaction equation

HRID 2195066 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[CH2:8]([O:10][C:11](=[O:20])[C:12]1[CH:17]=[C:16]([Cl:18])[C:15](Cl)=[N:14][CH:13]=1)[CH3:9].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[CH2:8]([O:10][C:11](=[O:20])[C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([N:6]2[CH2:5][CH2:4][NH:3][C@H:2]([CH3:1])[CH2:7]2)=[N:14][CH:13]=1)[CH3:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 73304342-Methylpiperazine, (R)-HCID 16762519Ethyl 5,6-Dichloronicotinate

Product 1

HCID 59168283HCID 59168283, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Heat a solution of (R)-2-methyl-piperazine (0.07 mol), 5,6-dichloro-nicotinic acid ethyl ester (TCI America) (10.1 g, 0.046 mol) and potassium carbonate (31.7 g, 0.23 mol) in DMA at 110° C. for 48 h. Cool the solution, and partition between EtOAc and brine. Separate the layers and extract the aqueous portion with EtOAc (1×). Wash the combined organic layers with 10% NaOH (4×), dry (Na2SO4), and concentrate under reduced pressure to give an oil which crystallizes on standing.

Workup

  1. temperatureCool the solution
  2. custompartition between EtOAc and brine
  3. customSeparate the layers
  4. extractionextract the aqueous portion with EtOAc (1×)
  5. washWash the combined organic layers with 10% NaOH (4×)
  6. dry with materialdry (Na2SO4)
  7. concentrationconcentrate under reduced pressure
  8. customto give an oil which
  9. customcrystallizes

Sources & evidence

ORD record
ord-5ce015a09c974b34b958f08ab9bdb661
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

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