cis-3,5-Dimethyl-1-[2-(methyloxy)-5-nitrophenyl]piperazine → 3-(cis-3,5-Dimethyl-1-piperazinyl)-4-(methyloxy)aniline

HRID 130398Notes

Reaction equation

HRID 130398 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=2[O:18][CH3:19])[CH2:3]1>[Pd].C(O)C.[H][H]>[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:14]=[C:13]([CH:12]=[CH:11][C:10]=2[O:18][CH3:19])[NH2:15])[CH2:3]1

Participants

5

Reactant 1

HCID 59007077cis-3,5-Dimethyl-1-[2-(methyloxy)-5-nitrophenyl]piperazine

Product 1

HCID 590070453-(cis-3,5-Dimethyl-1-piperazinyl)-4-(methyloxy)aniline

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

cis-3,5-Dimethyl-1-[2-(methyloxy)-5-nitrophenyl]piperazine (D1) (10 g, 38 mmol) and 10% palladium on charcoal were dissolved in ethanol (200 ml) and hydrogenated at room temperature under an atmosphere hydrogen for 16 hours. The mixture was filtered through celite and the filtrate concentrated in vacuo to afford the title product (D2). MS (ES+) m/e 236 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-56ad5d2fabca4eb5bb549ac683b051b9
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

Loading…