2-Methyl-5-(4-nitro-phenyl)-2,5-diaza-bicyclo[2.2.1]heptane → 4-(5-Methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)aniline

HRID 2236679Notes

Reaction equation

HRID 2236679 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]2[CH2:8][CH:3]1[CH2:4][N:5]2[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1>C(O)C.[Pd]>[CH3:1][N:2]1[CH2:7][CH:6]2[CH2:8][CH:3]1[CH2:4][N:5]2[C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 189990942-Methyl-5-(4-nitro-phenyl)-2,5-diaza-bicyclo[2.2.1]heptane

Product 1

HCID 594103234-(5-Methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)anilineYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-methyl-5-(4-nitro-phenyl)-2,5-diaza-bicyclo[2.2.1]heptane (0.19 g, 0.815 mmol) and a catalytic amount of Pd/C in ethanol (0.2 mL) is hydrogenated at 1 atmosphere at room temperature overnight. It is filtered through Celite, and the organic solution is evaporated, and then treated with 10 mL of methanol. It is then treated with hydrochloric acid in methanol, followed by ethyl ether, and filtered to give 4-(5-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-phenylamine as bluish solid (0.107 g, 65%). MS (ESI) m/z 204.2 (M−H)+1.

Workup

  1. filtrationIt is filtered through Celite
  2. customthe organic solution is evaporated
  3. additiontreated with 10 mL of methanol
  4. additionIt is then treated with hydrochloric acid in methanol
  5. filtrationfiltered

Sources & evidence

ORD record
ord-2bf3d366c2f04434b45b59c2921a33bb
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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