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

HRID 2236982

Reaction equation

HRID 2236982 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-0fe31491f29043a084b7f428bec089c9
Source dataset
uspto-grants-2010_05
Patent number
US07714013B2

Linked notes

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