Ethanol → 4-[2-(4-Methylpiperazin-1-yl)ethoxy]aniline

HRID 1261894Notes

Reaction equation

HRID 1261894 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH2:4][CH2:3]1.C(O)C>[Pd]>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 702EthanolHCID 128308431-Methyl-4-[2-(4-nitro-phenoxy)-ethyl]-piperazine

Product 1

HCID 230087924-[2-(4-Methylpiperazin-1-yl)ethoxy]anilineYield 68%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a Round bottom flask, 1-Methyl-4-[2-(4-nitro-phenoxy)-ethyl]-piperazine (3.89 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. The desired product was purified via ISCO column chromatography with DCM and methanol as eluant (0 to 10%). The collected fractions afforded 4-[2-(4-Methyl-piperazin-1-yl)-ethoxy]-phenylamine as a red solid (2.35 g, 68%). NMR 1H (DSMO-d6-6.63 (dd, 2H, JJ=1.92, 4.72 Hz), 6.48 (dd, 2H, JJ=1.96, 4.72 Hz), 4.52 (bs, 2H), 3.89 (t, 2H, J=5.92 Hz), 2.59 (t, 2H, J=5.92 Hz), 2.44 (bs, 4H), 2.29 (bs, 4H), 2.13 (s, 3H)

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
  5. customThe desired product was purified via ISCO column chromatography with DCM and methanol as eluant (0 to 10%)

Sources & evidence

ORD record
ord-d4cbc50ef139431893ee4f87c51d17aa
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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