1-(4-Bromo-3-nitrophenyl)-4-methylpiperazine → 2-Bromo-5-(4-methylpiperazin-1-yl)phenylamine

HRID 1358938Notes

Reaction equation

HRID 1358938 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[N+:15]([O-])=O>[Cl-].[NH4+].CO.[Fe]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)=[CH:4][C:3]=1[NH2:15]

Participants

5

Reactant 1

HCID 181801571-(4-Bromo-3-nitrophenyl)-4-methylpiperazine

Product 1

HCID 181800752-Bromo-5-(4-methylpiperazin-1-yl)phenylamineYield 68.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A suspension of iron powder (1.77 g, 31.6 mmol) in saturated aqueous ammonium chloride solution (140 ml) at 100° C., was treated dropwise with a solution of 1-(4-bromo-3-nitrophenyl)-4-methylpiperazine (D26) (3.54 g, 11.8 mmol) in methanol (70 ml). The mixture was refluxed for a further 1 h, and was then cooled and partitioned between water and 3% methanol in dichloromethane. The organic phase was dried (Na2SO4) and evaporated under reduced pressure to give the crude product. This was purified by chromatography on silica gel, eluting with methanol and dichloromethane to give the title compound (D27) as a white solid (2.18 g, 68%) MH+=270/272.

Workup

  1. temperatureThe mixture was refluxed for a further 1 h
  2. temperaturewas then cooled
  3. custompartitioned between water and 3% methanol in dichloromethane
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customto give the crude product
  7. customThis was purified by chromatography on silica gel
  8. washeluting with methanol and dichloromethane

Sources & evidence

ORD record
ord-1e99a4d3cbf843e78ab90a06f514367a
Source dataset
uspto-grants-2003_07
Patent number
US06599904B2

Reaction notes

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