2-Bromo-5-nitropyridine → tert-Butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylate

HRID 1021900Notes

Reaction equation

HRID 1021900 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[N:11]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>C(#N)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:14]2[CH2:13][CH2:12][N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 782402-Bromo-5-nitropyridineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 16217943tert-Butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylateYield 54.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromo-5-nitropyridine (5.0 g, 24.6 mmol), tert-butyl piperazine-1-carboxylate (13.8 g, 74.2 mmol), acetonitrile (150 mL) was stirred at reflux for 2.5 h. After the reaction was completed, the solvent was removed under reduced pressure to afford 197a as a yellow solid (4.1 g, 54%). MS-ESI: [M+H]+ 309.

Workup

  1. temperatureat reflux for 2.5 h
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3f6de6fc0ff941999820118658d615f8
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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