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

HRID 1042702Notes

Reaction equation

HRID 1042702 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1>C(O)C.[Pd]>[CH3:16][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1

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

4-(3-(dimethylamino)propoxy)nitrobenzene (4.4 g, 19.6 mmol) was hydrogenated over Pd (10% on C, 0.4 g) in ethanol (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. MS (m/z)=195.3 (M+H+); Calc'd for C11H18N2O=194.28.

Workup

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

Sources & evidence

ORD record
ord-6c8632bc0a114664b7a78dd0642bbe76
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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