Piperazine → 1-(5-Methyl-2-pyridinyl)piperazine

HRID 1961672Notes

Reaction equation

HRID 1961672 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 5642162-Bromo-5-methylpyridine

Product 1

HCID 114807791-(5-Methyl-2-pyridinyl)piperazine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of piperazine (215 mg, 2.5 mmoles), 2-bromo-5-methyl-pyridine (172 mg, 1 mmoles) in dioxane (1 mL) and potassium carbonate (276 mg, 2 mmoles) was irradiated by microwaves for 60 minutes at 180° C. The dioxane was removed under reduced pressure and the residue partitioned between aqueous potassium carbonate and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic extracts washed twice with water, dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the residue was purified (silica gel, 0-10% methanol in dichloromethane) to provide the title compound as a white solid.

Workup

  1. customThe dioxane was removed under reduced pressure
  2. customthe residue partitioned between aqueous potassium carbonate and ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic extracts washed twice with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified (silica gel, 0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-92cfec460be64ab1862643c06ff1e519
Source dataset
uspto-grants-2013_04
Patent number
US08415354B2

Reaction notes

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