Water → 4-Boc-1-(6-bromo-2-pyridyl)piperazine

HRID 403205Notes

Reaction equation

HRID 403205 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[N:9]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:8][C:4]1[N:3]=[C:2]([N:12]2[CH2:11][CH2:10][N:9]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13]2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 122742,6-DibromopyridineHCID 143452tert-Butyl piperazine-1-carboxylate2×

Product 1

HCID 160590464-Boc-1-(6-bromo-2-pyridyl)piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-Dibromopyridine (1.0 g) and tert-butyl piperazine-1-carboxylate (870 mg) are dissolved in N,N-dimethylformamide (10 ml) and stirred at 80° C. in the presence of potassium carbonate (1.17 g) for 5 hours. To the reaction mixture is added tert-butyl piperazine-1-carboxylate (200 mg). The mixture is stirred at room temperature overnight, and then water is added. The aqueous phase is removed and extracted with dichloromethane. The combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. The residue is purified by chromatography. This gives tert-butyl 4-(6-bromopyridin-2-yl)piperazine-1-carboxylate (900 mg).

Workup

  1. customThe aqueous phase is removed
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-c55759ddd1704221a96a3a30e26db720
Source dataset
uspto-grants-2014_06
Patent number
US08748420B2

Reaction notes

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