Potassium Carbonate → 1-(2-Pyridyl)piperazine

HRID 230970Notes

Reaction equation

HRID 230970 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 27342192-Methylpiperazine, (S)-

Product 1

HCID 944591-(2-Pyridyl)piperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

Dissolve 2,3-dichloropyridine (7.4 g, 0.05 moles) and (S)-(−)-2-methylpiperazine (5.0 g, 0.05 moles) in DMA (125.0 mL) under nitrogen atmosphere. Add anhydrous powdered K2CO3 (20.75 g, 0.15 moles) to this mixture and stir at 135-140° C. for 56 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, and concentrate under vacuum to afford crude product as yellow liquid. Purify by flash column chromatography using CHCl3 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 yellow liquid
  7. customPurify by flash column chromatography

Sources & evidence

ORD record
ord-e02010b6877f430cb3d58b1d391b7b0e
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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