9-(Phenylmethyl)-9-azabicyclo[3.3.1]nonan-3-one oxime → 9-Benzyl-9-azabicyclo[3.3.1]nonan-3-amine
Reaction equation
[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH2:16][CH:9]1[CH2:10][C:11](=[N:17]O)[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Ni]>[NH2:17][CH:11]1[CH2:10][CH:9]2[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:13]([CH2:14][CH2:15][CH2:16]2)[CH2:12]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
9-Benzyl-9-azabicyclo-(3.3.1)-nonan-3-one oxime (4.0 g; 0.0164 mole), m.p. 134°, was dissolved in ethanol (100 ml) and hydrogenated at 50°-60° at 250 psi in the presence of Raney nickel. The mixture was filtered after 24 hours through kieselguhr and evaporated in vacuo. The resulting oil was dissolved in dilute hydrochloric acid (50 ml) extracted with ethyl acetate (3×150 ml), the aqueous layer was basified and re-extracted with ethyl acetate (3×150 ml). The combined organic extracts were dried (K2CO3), filtered and evaporated in vacuo to yield 3-amino-9-benzyl-9-azabicyclo-[3.3.1]-nonane (2.3 g; 61%), used without further purification.