Potassium Carbonate → 1-(2-Pyridyl)piperazine

HRID 230963Notes

Reaction equation

HRID 230963 reaction equation
Cl[C:2]1[C:7](Cl)=[CH:6][CH:5]=[CH:4][N:3]=1.C[C@@H:10]1[CH2:15][NH:14][CH2:13][CH2:12][NH:11]1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O.O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:10]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 169882,3-DichloropyridineHCID 73304342-Methylpiperazine, (R)-

Product 1

HCID 944591-(2-Pyridyl)piperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

Dissolve 2,3-dichloropyridine (8.5 g, 0.057 moles) and (R)-(−)-2-methylpiperazine (5.75 g, 0.057 moles) in DMA(125.0 mL) under nitrogen atmosphere. Add anhydrous powdered K2CO3 (23.75 g, 0.172 moles) to this mixture and stir at 135-140° C. for 48 hours. Cool the reaction mixture to room temperature, dilute with water (400 mL), extract with EtOAc (3×200 mL) and wash the combined organic extract with brine (2×150 mL). Dry over MgSO4, concentrate under vacuum to afford crude product as orange yellow liquid. Distil the crude under high vacuum to afford pyridylpiperazine derivative as yellow viscous oil.

Workup

  1. extractionextract with EtOAc (3×200 mL)
  2. washwash the combined
  3. extractionorganic extract with brine (2×150 mL)
  4. dry with materialDry over MgSO4
  5. concentrationconcentrate under vacuum
  6. customto afford crude product as orange yellow liquid
  7. customDistil the crude under high vacuum

Sources & evidence

ORD record
ord-935eed6fff2a4278aba0f6318f10bc88
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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