1-(4-Methoxy-3-nitrophenyl)-4-methylpiperazine → HCID 24994141, compound

HRID 1014218Notes

Reaction equation

HRID 1014218 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([N+:16]([O-])=O)[CH:9]=2)[CH2:4][CH2:3]1>C(O)C.[Pd]>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[CH:9][C:10]=1[NH2:16]

Participants

4

Reactant 1

HCID 594418861-(4-Methoxy-3-nitrophenyl)-4-methylpiperazine

Product 1

HCID 24994141HCID 24994141, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-methyl-4-[4-(methyloxy)-3-nitrophenyl]piperazine (0.25 g, 1.0 mmol) in absolute ethanol (100 mL) was hydrogenated with 10% Pd/C at 50 psi overnight. The catalyst was removed by vacuum filtration through a celite pad, rinsed with methanol, filtrate was concentrated under reduced pressure, and the crude aniline was purified by chromatography on SiO2 (dichloromethane to 10% methanol/dichloromethane with 0.1% NH4OH) to afford 2-(methyloxy)-5-(4-methyl-1-piperazinyl)aniline (0.19 g, 85%) as a tan solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.35 (s, 3 H) 2.55-2.64 (m, 4 H) 3.06-3.13 (m, 4 H) 3.78 (s, 3 H) 6.29 (dd, J=8.61, 2.75 Hz, 1 H) 6.38 (d, J=2.75 Hz, 1 H) 6.69 (d, J=8.61 Hz, 1 H). ESIMS (M+H)+=222.

Workup

  1. customThe catalyst was removed by vacuum filtration through a celite pad
  2. washrinsed with methanol, filtrate
  3. concentrationwas concentrated under reduced pressure
  4. customthe crude aniline was purified by chromatography on SiO2 (dichloromethane to 10% methanol/dichloromethane with 0.1% NH4OH)

Sources & evidence

ORD record
ord-2e2c6e6e3df5416bb8e437e01e6cb559
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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