Ethanol → 4-[3-(4-Methylpiperazin-1-yl)propoxy]aniline

HRID 1261911Notes

Reaction equation

HRID 1261911 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[CH2:4][CH2:3]1.C(O)C>[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 702EthanolHCID 574161581-Methyl-4-[3-(4-nitrophenoxy)propyl]piperazine

Product 1

HCID 221246044-[3-(4-Methylpiperazin-1-yl)propoxy]aniline

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a Round bottom flask, 1-Methyl-4-[3-(4-nitro-phenoxy)-propyl]-piperazine (4.10 g, 0.0147 mol), 10% Pd/C (10:90, Palladium:carbon black, 1.6 g, 0.0015 mol), and Ethanol (100 mL, 2 mol) were added. The mixture was evacuated under house vacuum and charged with a hydrogen balloon (3×). The reaction was stirred at room temperature under an atmosphere of Hydrogen via a balloon. The solid was filtered. The solvent was removed under vacuum to give 4-[3-(4-Methyl-piperazin-1-yl)-propoxy]-phenylamine a white solid (2.86, 78%). 1H (DSMO-d6)-6.62 (dd, 1H, J=2.08, 4.57 Hz), 6.49 (dd, 2H, J=2.16, 5.64 Hz), 4.56 (bs, 2H), 3.82 (t, 2H, J=6.40 Hz), 2.20-2.45 (m, 10H), 2.13 (s, 3H), 1.70-1.83 (m, 2H)

Workup

  1. customThe mixture was evacuated under house vacuum
  2. additioncharged with a hydrogen balloon (3×)
  3. filtrationThe solid was filtered
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-2ef9fe69d4cc43cead280d7d3950d0ae
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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