1-(1-Methylethyl)-4-[2-methyl-3-(methyloxy)-4-nitrophenyl]piperazine → 3-Methyl-4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)aniline

HRID 1014260Notes

Reaction equation

HRID 1014260 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])[C:11]=2[CH3:21])[CH2:6][CH2:5]1)[CH3:3]>CO.[Ni]>[CH3:21][C:11]1[C:12]([O:19][CH3:20])=[C:13]([CH:14]=[CH:15][C:10]=1[N:7]1[CH2:6][CH2:5][N:4]([CH:2]([CH3:3])[CH3:1])[CH2:9][CH2:8]1)[NH2:16]

Participants

4

Reactant 1

HCID 594417791-(1-Methylethyl)-4-[2-methyl-3-(methyloxy)-4-nitrophenyl]piperazine

Product 1

HCID 594419603-Methyl-4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)anilineYield 91.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-(1-methylethyl)-4-[2-methyl-3-(methyloxy)-4-nitrophenyl]piperazine (5.5 g, 18.7 mmol) and Raney Ni (2 g) in 200 mL of MeOH was stirred under an atmosphere of H2 overnight. The mixture was filtered and taken to a residue under reduced pressure to afford 3-methyl-4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)aniline as a white solid (4.50 g, 91% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.10 (d, J=6.4 Hz, 6H), 2.24 (s, 3H), 2.73-2.67 (m, 5H), 2.89 (m, 4H), 3.63 (s, 2H), 3.73 (s, 3H), 6.58 (d, J=8.4 Hz, 1H), 6.71 (d, J=8.4 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-ccd66e9f2b4a4c56bb05f4c7ff9b312e
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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