N,N-diethyl-N-[3-(3-nitrophenoxy)propyl]amine → N-[3-(3-aminophenoxy)propyl]-N,N-diethylamine

HRID 17659

Reaction equation

HRID 17659 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)[CH3:2]>CO.[Pd]>[NH2:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[O:7][CH2:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:17][CH3:18]

Participants

4

Reactant 1

HCID 22012884N,N-diethyl-N-[3-(3-nitrophenoxy)propyl]amine

Product 1

HCID 28300924N-[3-(3-aminophenoxy)propyl]-N,N-diethylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The N,N-diethyl-N-[3-(3-nitrophenoxy)propyl]amine (1 mmol) was dissolved in MeOH (5 mL) and hydrogenated in the presence of 10% Pd/C (50 mg) until completion as indicated by TLC or HPLC, according to General Procedure H. The reaction mixture was then filtered to remove the catalyst. The solvent was removed in vacuuo to afford the desired N-[3-(3-aminophenoxy)propyl]-N,N-diethylamine, which was used directly for further transformation without further purification.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customto remove the catalyst
  3. customThe solvent was removed in vacuuo

Sources & evidence

ORD record
ord-7a0fcccdeb344ea994fe2adf34712ddf
Source dataset
uspto-grants-2010_06
Patent number
US07737285B2

Linked notes

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