1-Bromo-2-nitrobenzene → HCID 7060194, compound

HRID 1066981Notes

Reaction equation

HRID 1066981 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][C@@H:12]1[CH2:17][NH:16][CH2:15][CH2:14][NH:13]1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[CH3:11][C@H:12]1[NH:13][CH2:14][CH2:15][N:16]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:17]1

Participants

5

Reactant 3

HCID 113411-Bromo-2-nitrobenzeneHCID 11430Potassium CarbonateHCID 73304342-Methylpiperazine, (R)-

Product 1

HCID 7060194HCID 7060194, compoundYield 470%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-bromo-nitrobenzene (0.4 g, 2.0 mmol) in 1,4-dioxane (10 mL) was added (R)-(+)-2-methylpiperazine (0.25 g, 0.25 mmol) and powdered K2CO3 (7.5 mmol, 0.8 g) and the resulting suspension was heated at reflux for 10 h. After the suspension was cooled, it was filtered through a sintered glass funnel and the solvent was evaporated in vacuo. The resulting residue was purified by column chromatography on silica gel (1:1 hexane/EtOAc followed by 4:1 EtOAc/MeOH) to yield (R)-(+)-3-methyl-1-(2-nitrophenyl)-piperazine as an orange-red oil (0.26 g, 78%).

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureat reflux for 10 h
  3. temperatureAfter the suspension was cooled
  4. filtrationit was filtered through a sintered glass funnel
  5. customthe solvent was evaporated in vacuo
  6. customThe resulting residue was purified by column chromatography on silica gel (1:1 hexane/EtOAc followed by 4:1 EtOAc/MeOH)

Sources & evidence

ORD record
ord-55775919c6c547e6833c6daf3c07da9f
Source dataset
uspto-grants-2001_06
Patent number
US06245773B1

Reaction notes

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