1-Bromo-2-nitrobenzene → HCID 7060196, compound

HRID 2085437Notes

Reaction equation

HRID 2085437 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 27342192-Methylpiperazine, (S)-

Product 1

HCID 7060196HCID 7060196, compoundYield 479.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-bromonitrobenzene (0.600 g, 3.00 mmol) in 1,4-dioxane (15 mL) was added (S)-(+)-2-methylpiperazine (0.500 g, 0.500 mmol) and powdered K2CO3 (15.0 mmol, 1.50 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 removed in vacuo. The resulting residue was purified by column chromatography (1/1 hexane/EtOAc followed by 4/1 EtOAc/MeOH), giving (S)-(+)-3-methyl-1-(2-nitrophenyl)-piperazine as an orange oil (0.53 g, 80%).

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 removed in vacuo
  6. customThe resulting residue was purified by column chromatography (1/1 hexane/EtOAc followed by 4/1 EtOAc/MeOH)

Sources & evidence

ORD record
ord-3f0c44b9e7554bf78993c4a74096742a
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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