1-(1-Methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]piperazine → 4-(4-Isopropylpiperazin-1-YL)-2-methoxyphenylamine

HRID 1014202Notes

Reaction equation

HRID 1014202 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([O:19][CH3:20])[CH:11]=2)[CH2:6][CH2:5]1)[CH3:3]>CCO>[CH3:3][CH:2]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([O:19][CH3:20])[CH:11]=2)[CH2:8][CH2:9]1)[CH3:1]

Participants

3

Reactant 1

HCID 587484431-(1-Methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]piperazine

Product 1

HCID 457907394-(4-Isopropylpiperazin-1-YL)-2-methoxyphenylamineYield 101%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a pressure vessel was placed a solution of 1-(1-methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]piperazine (4.0 g, 14.3 mmol) in EtOH (100 mL). The solution was purged with N2 for 15 min before the addition of 10% Pd/C (0.5 g). The reaction was stirred at RT for 5 h under 60 psi H2. After releasing H2 pressure, filtration removed the solid resin, and the filtrate was concentrated and purified with silica gel chromatography (0-5% 2 M NH3 in MeOH/DCM) to furnish 4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)aniline (3.6 g, 99% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.09 (d, J=6.6 Hz, 6 H), 2.66-2.75 (m, 5 H), 3.05-3.10 (m, 4 H), 3.47 (s, 3 H), 3.83 (s, 2 H), 6.42 (dd, J=8.2, 2.4 Hz, 1 H), 6.52 (d, J=2.2 Hz, 1 H), 6.64 (d, J=8.4 Hz, 1 H).

Workup

  1. customIn a pressure vessel was placed
  2. customThe solution was purged with N2 for 15 min before the addition of 10% Pd/C (0.5 g)
  3. filtrationH2 pressure, filtration
  4. customremoved the solid resin
  5. concentrationthe filtrate was concentrated
  6. custompurified with silica gel chromatography (0-5% 2 M NH3 in MeOH/DCM)

Sources & evidence

ORD record
ord-0268b6858ade427da63765676392c2e6
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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