Pyridine → 1-(5-Bromo-4-methyl-pyridin-2-yl)-4-isopropyl-piperazine

HRID 80917Notes

Reaction equation

HRID 80917 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[CH:4][N:3]=1.[CH:10]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:12])[CH3:11].N1C=CC=CC=1>[Cl-].[Na+].O>[Br:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([N:16]2[CH2:17][CH2:18][N:13]([CH:10]([CH3:12])[CH3:11])[CH2:14][CH2:15]2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 780131-IsopropylpiperazineHCID 27344292,5-Dibromo-4-methylpyridine

Product 1

HCID 580066171-(5-Bromo-4-methyl-pyridin-2-yl)-4-isopropyl-piperazineYield 90.5%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2,5-dibromo-4-methyl-pyridine (5.0 g, 20 mmol) and isopropyl-piperazine (25.6 g, 200 mmol) were added pyridine (2.06 g, 206 mmol). The reaction mixture was refluxed for 5 h under a nitrogen atmosphere. Brine was added and the mixture was extracted with EtOAc. The organic extract was washed with brine and 0.5 N hydrochloric acid. The acidic layer was made alkaline with Na2CO3 to pH 8 and then extracted with CH2Cl2. The organic extract was dried (Na2SO4) and concentrated to give 5.4 g (90%) of 1-(5-bromo-4-methyl-pyridin-2-yl)-4-isopropyl-piperazine.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h under a nitrogen atmosphere
  2. extractionthe mixture was extracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine and 0.5 N hydrochloric acid
  5. extractionextracted with CH2Cl2
  6. extractionThe organic extract
  7. dry with materialwas dried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b3401f3ad6d449b082aac31219cadcb2
Source dataset
uspto-grants-2014_09
Patent number
US08846677B2

Reaction notes

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