2,5-Dibromopyridine → 1-(5-Bromopyridin-2-yl)-4-(propan-2-yl)piperazine

HRID 1726873Notes

Reaction equation

HRID 1726873 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH:9]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)([CH3:11])[CH3:10].C1CCN2C(=NCCC2)CC1>O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:15]2[CH2:16][CH2:17][N:12]([CH:9]([CH3:11])[CH3:10])[CH2:13][CH2:14]2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 693532,5-DibromopyridineHCID 780131-IsopropylpiperazineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 199958461-(5-Bromopyridin-2-yl)-4-(propan-2-yl)piperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution containing 12.1 g of 2,5-dibromopyridine (51.1 mmol), 8.8 ml of 1-isopropylpiperazine (61.5 mmol) and 9.2 ml of DBU (61.5 mmol) is stirred overnight at 100° C. The reaction mixture is returned to ambient temperature and the solution is diluted with water and extracted with ethyl acetate. The organic phases are collected, washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue is chromatographed on an SiO2 column, eluting with a mixture of CH2Cl2/MeOH 98/2 and then 96/4, to yield the title product.

Workup

  1. customis returned to ambient temperature
  2. extractionextracted with ethyl acetate
  3. customThe organic phases are collected
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customThe residue is chromatographed on an SiO2 column
  8. washeluting with a mixture of CH2Cl2/MeOH 98/2

Sources & evidence

ORD record
ord-e240ed1691f74b2eb57b46dcd73a987c
Source dataset
uspto-grants-2009_02
Patent number
US07494995B2

Reaction notes

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