Tetrahydrofuran → 4-[4-(2-Methoxy-ethyl)-piperazin-1-yl]-3-methyl-phenylamine

HRID 469832Notes

Reaction equation

HRID 469832 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:12]=2[CH3:20])[CH2:7][CH2:6]1.C1COCC1>CO.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=2[CH3:20])[CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 674588251-(2-Methoxy-ethyl)-4-(2-methyl-4-nitro-phenyl)-piperazine

Product 1

HCID 666173884-[4-(2-Methoxy-ethyl)-piperazin-1-yl]-3-methyl-phenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.85 g (3.04 mmol) 1-(2-methoxy-ethyl)-4-(2-methyl-4-nitro-phenyl)-piperazine in 20 ml MeOH:THF=1:1 is hydrogenated in the presence of 0.2 g 10% Pd/C (Engelhard 4505). The reaction mixture is filtered (2 glass fiber filters used) and the filtrate is concentrated in vacuo to afford the title compound as an oil.

Workup

  1. filtrationThe reaction mixture is filtered (2 glass fiber filters used)
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-5cf1bcbbf98a4561a3630887a21c097b
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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