N,N-dimethyl-3-(4-nitrophenoxy)propan-1-amine → 4-(3-(Dimethylamino)propoxy)aniline

HRID 2117620Notes

Reaction equation

HRID 2117620 reaction equation
[CH3:1][N:2]([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)[CH3:3]>C(O)C.[Pd]>[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1)[CH3:3]

Participants

4

Reactant 1

HCID 10353575N,N-dimethyl-3-(4-nitrophenoxy)propan-1-amine

Product 1

HCID 100584694-(3-(Dimethylamino)propoxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N,N-dimethyl-3-(4-nitrophenoxy)propylamine (4.4 g, 19.6 mmol) was hydrogenated over Pd (10% on C, 0.4 g) in ethanol (ca 50 mL) for 16 h. The catalyst was filtered off and the solvent removed under reduced pressure to afford the title compound as a brown oil. 1H NMR (400 MHz, dmso-d6): 1.95 (2H, t, J 6.5 Hz); 2.25 (6H, s); 2.35-2.45 (2H, m); 3.95 (2H, t, J 6.5 Hz); 4.7 (2H, bs); 6.9 (2H, d, J 8 Hz); 8.1 (2H, d, J 8 Hz); 6.65 (2H, d, J 8 Hz); 6.75 (2H, d, J 8 Hz).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-948947b0bcd146a08ee0cb2ec27595d8
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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