Piperazine → 1-(2-Nitrophenyl)piperazine

HRID 324314Notes

Reaction equation

HRID 324314 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 4837PiperazineHCID 113411-Bromo-2-nitrobenzene

Product 1

HCID 1009491-(2-Nitrophenyl)piperazineYield 92%

Conditions

Temperature
100 °C

Procedure

A heterogenous reaction mixture containing 2-bromonitrobenzene (2.02 g, 10.0 mmol) and piperazine (4.3 g, 50.0 mmol) was heated at 100° C. for 10 hours. The orange-red solid was extracted with ethyl acetate and washed thoroughly with 3 N NaOH solution followed by brine. The organic layer was separated and dried over Na2SO4, filtered and the solvent was removed in vacuo. The resulting red oil was purified by column chromatography on silica gel (1:1 hexane/EtOAc followed by 4:1 EtOAc/MeOH) to yield 1-(2-nitrophenyl)piperazine as an orange-red oil (1.90 g, 92%). It was characterized as a hydrochloride salt. Analysis calculated for C10H14N3O2Cl.0.10. CHCl3: C, 47.46; H. 5.56; N, 16.44. Found: C, 47.63; H. 5.69; N, 16.42.

Workup

  1. extractionThe orange-red solid was extracted with ethyl acetate
  2. washwashed thoroughly with 3 N NaOH solution
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe resulting red oil was purified by column chromatography on silica gel (1:1 hexane/EtOAc followed by 4:1 EtOAc/MeOH)

Sources & evidence

ORD record
ord-a1a76073f1444dcabd2207458457dddc
Source dataset
uspto-grants-2001_04
Patent number
US06218390B1

Reaction notes

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