2,5-Dibromo-3-methylpyridine → 1-(5-Bromo-3-methyl-pyridin-2-yl)-3-(R)-methyl-piperazine

HRID 2195086Notes

Reaction equation

HRID 2195086 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[CH3:10][C@@H:11]1[CH2:16][NH:15][CH2:14][CH2:13][NH:12]1>CC(N(C)C)=O>[Br:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([N:15]2[CH2:14][CH2:13][NH:12][C@H:11]([CH3:10])[CH2:16]2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 8176802,5-Dibromo-3-methylpyridineHCID 73304342-Methylpiperazine, (R)-

Product 1

HCID 574734721-(5-Bromo-3-methyl-pyridin-2-yl)-3-(R)-methyl-piperazine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Heat a solution of 2,5-dibromo-3-methyl-pyridine (Chontech Inc., Waterford, Conn.) (2.0 g, 7.97 mmol), (R)-2-methyl-piperazine (ChemPacific Corp., Baltimore, Md.; 3.2 g, 31.9 mmol) in DMA at 130° C. for 16 h. Partition the reaction mixture between water and EtOAc. Wash the EtOAc layer with water (1×) and brine (1×), dry (Na2SO4) and concentrate under reduced pressure to give 1-(5-bromo-3-methyl-pyridin-2-yl)-3-(R)-methyl-piperazine as a solid.

Workup

  1. customPartition the reaction mixture between water and EtOAc
  2. washWash the EtOAc layer with water (1×) and brine (1×)
  3. dry with materialdry (Na2SO4)
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-a43f2b9417764a328580bff230ff6687
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

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