Ethyl Acetate → Tert-butyl 4-(6-bromopyridin-3-yl)piperazine-1-carboxylate

HRID 1465458Notes

Reaction equation

HRID 1465458 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH:2]=1.[Br:20]N1C(=O)CCC1=O.[OH-].[Na+].C(OCC)(=O)C>C(#N)C>[Br:20][C:6]1[N:1]=[CH:2][C:3]([N:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 11673373Tert-butyl 4-(pyridin-3-YL)piperazine-1-carboxylate

Product 1

HCID 11530243Tert-butyl 4-(6-bromopyridin-3-yl)piperazine-1-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl 4-pyridin-3-ylpiperazine-1-carboxylate (1.0 g, 3.80 mmol) in acetonitrile (12 ml) was added N-bromosuccinimide (676 mg, 3.80 mmol) by small portions at room temperature. After stirring at room temperature for 1.5 hrs, the reaction mixture was poured into a mixture of 1M aqueous sodium hydroxide solution and ethyl acetate. The mixture was stirred, stood still and partitioned. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give tert-butyl 4-(6-bromopyridin-3-yl)piperazine-1-carboxylate (1.26 g, yield 97%).

Workup

  1. stirringThe mixture was stirred
  2. custompartitioned
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9293f40ed50b45758df8155e4b119ea8
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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