1-Methyl-4-(4-nitrophenyl)-1,4-diazepane → 4-(4-Methyl-1,4-diazepan-1-yl)aniline

HRID 2236695Notes

Reaction equation

HRID 2236695 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1>C(O)C.[Pd]>[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 31247221-Methyl-4-(4-nitrophenyl)-1,4-diazepane

Product 1

HCID 130079514-(4-Methyl-1,4-diazepan-1-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution 1-methyl-4-(4-nitrophenyl)-1,4-diazepane in ethanol is hydrogenated overnight at atmospheric pressure over 10% Pd/C. The mixture is filtered through a pad of diatomaceous earth and concentrated under reduced pressure to give 4-(4-methyl-[1,4]-diazepan-1-yl)phenylamine as a dark maroon oil.

Workup

  1. filtrationThe mixture is filtered through a pad of diatomaceous earth
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e32bfe369953471bbb0f5579b3eddeae
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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