HCID 59442053, compound → HCID 59441839, compound

HRID 1014220Notes

Reaction equation

HRID 1014220 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([N+:18]([O-])=O)[CH:11]=2)[CH2:6][CH2:5]1)[CH3:3]>C(O)C.[Pd]>[CH3:3][CH:2]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([CH:11]=2)[NH2:18])[CH2:8][CH2:9]1)[CH3:1]

Participants

4

Reactant 1

HCID 59442053HCID 59442053, compound

Product 1

HCID 59441839HCID 59441839, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(1-methylethyl)-4-[4-(methyloxy)-3-nitrophenyl]piperazine (0.6 g, 2.15 mmol) in absolute ethanol (100 mL) was hydrogenated with 10% Pd/C (Lancaster) at 50 psi overnight. The catalyst was removed by vacuum filtration through a celite pad, rinsed with methanol, the 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 provide 5-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)aniline as a white solid (0.42 g, 80%). ESIMS (M+H)+=250.

Workup

  1. customThe catalyst was removed by vacuum filtration through a celite pad
  2. washrinsed with methanol
  3. concentrationthe filtrate was 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-ccd1f54ebca74263a8b0528cb6e8dd46
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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