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

HRID 1167699Notes

Reaction equation

HRID 1167699 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-bromo-nitrobenzene (0.6 g, 3.0 mmol) in 1,4-dioxane (15 mL) was added (S)-(+)-2-methylpiperazine (0.5 g, 0.5 mmol) and powdered K2CO3 (15.0 mmol, 1.5 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 (S)-(+)-3-methyl-1-(2-nitrophenyl)-piperazine as an orange oil (0.53 g, 80%). It was converted into (S)-(+)-3-methyl-1-(2-nitrophenyl)-4-(3-aminopropyl)-piperazine by the usual procedure.

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-83cac71d05704183a2da05d351891198
Source dataset
uspto-grants-2003_09
Patent number
US06620815B1

Reaction notes

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