1-(4-(3-Methoxy-4-nitrophenyl)piperazin-1-yl)ethanone → 1-(4-(4-aMino-3-Methoxyphenyl)piperazin-1-yl)ethanone

HRID 527439Notes

Reaction equation

HRID 527439 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:20])[CH3:19])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.[H][H]>CCO.[Pd]>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([N:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:20])[CH3:19])[CH2:14][CH2:13]2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 594418231-(4-(3-Methoxy-4-nitrophenyl)piperazin-1-yl)ethanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 552327371-(4-(4-aMino-3-Methoxyphenyl)piperazin-1-yl)ethanoneYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(4-(3-methoxy-4-nitrophenyl)piperazin-1-yl)ethanone (20a) in 10 mL of EtOH was hydrogenated with a balloon filled with hydrogen in the presence of palladium (10 wt. % on activated carbon, 0.61 g, 0.57 mmol) for 18 h at RT. It was filtered through a pad of Celite and rinsed with EtOAc (2×20 mL). The filtrate was concentrated. The brown residue was triturated with 10 mL of hexanes. The liquid was decanted. The solid was dried in a vacuum oven at 40° C. for 1 h to give 1-(4-(4-amino-3-methoxyphenyl)piperazin-1-yl)ethanone (20b; 1.42 g, 5.70 mmol, 99% yield) as a brown solid. Crude material used in the next step. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.54 (2H, m), 6.32 (1H, dd, J=8.3, 2.4 Hz), 4.63 (2H, br.), 3.76 (3H, s), 3.54 (4H, m), 2.95 (2H, m), 2.89 (2H, m), 2.02 (3H, s). m/z (ESI, +ve ion) 250.1 (M+H)+.

Workup

  1. filtrationIt was filtered through a pad of Celite
  2. washrinsed with EtOAc (2×20 mL)
  3. concentrationThe filtrate was concentrated
  4. customThe brown residue was triturated with 10 mL of hexanes
  5. customThe liquid was decanted
  6. customThe solid was dried in a vacuum oven at 40° C. for 1 h

Sources & evidence

ORD record
ord-34595e1930e944a68ec122354091ba01
Source dataset
uspto-grants-2016_05
Patent number
US09346801B2

Reaction notes

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