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

HRID 1361424Notes

Reaction equation

HRID 1361424 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-6e208406aeac4e65a812c84dd2543b27
Source dataset
uspto-grants-2011_02
Patent number
US07880001B2

Reaction notes

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