N,N-diethyl-3-(4-nitrophenoxy)propan-1-amine → 4-[3-(diethylamino)propoxy]Benzenamine

HRID 17687Notes

Reaction equation

HRID 17687 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][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)[CH3:2]>CO.[Pd]>[CH2:1]([N:3]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1)[CH2:17][CH3:18])[CH3:2]

Participants

4

Reactant 1

HCID 2057886N,N-diethyl-3-(4-nitrophenoxy)propan-1-amine

Product 1

HCID 198634024-[3-(diethylamino)propoxy]Benzenamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The N,N-diethyl-N-[3-(4-nitrophenoxy)propyl]amine (2 mmol) obtained above was dissolved in MeOH (10 mL) and hydrogenated in the presence of 10% Pd/C (10 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 4-(N,N-diethylaminopropoxy)aniline, 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-38ab10c6f58f4a3eb200abb3ae56304f
Source dataset
uspto-grants-2010_06
Patent number
US07737285B2

Reaction notes

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