8-Benzyl-N-(2-nitrophenyl)-8-azabicyclo[3.2.1]octan-3-amine → N-(8-Benzyl-8-azabicyclo[3.2.1]oct-3-yl)benzene-1,2-diamine

HRID 1992047Notes

Reaction equation

HRID 1992047 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-])=O)[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.CO.[Pd]>[CH2:1]([N:8]1[CH:9]2[CH2:15][CH2:14][CH:13]1[CH2:12][CH:11]([NH:16][C:17]1[C:18]([NH2:23])=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:10]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 185070268-Benzyl-N-(2-nitrophenyl)-8-azabicyclo[3.2.1]octan-3-amine

Product 1

HCID 21132356N-(8-Benzyl-8-azabicyclo[3.2.1]oct-3-yl)benzene-1,2-diamineYield 79.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.92 g (9.04 mmol) 8-benzyl-N-(2-nitrophenyl)-8-azabicyclo[3.2.1]octan-3-amine was dissolved in 150 ml EtOAc and 25 ml Methanol. 1 g Pd/C was then added and the mixture was stirred at 1 atm H2 for 3.5 hrs. Yellow color disappeared and the reaction mixture was filtered through celite. The solvent was removed to afford 2.2 g of desired solid.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-92f95448202a4fbdb078198c3da7647c
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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