9-(Phenylmethyl)-9-azabicyclo[3.3.1]nonan-3-one oxime → 9-Benzyl-9-azabicyclo[3.3.1]nonan-3-amine

HRID 1680433Notes

Reaction equation

HRID 1680433 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]1

Participants

4

Reactant 1

HCID 28225629-(Phenylmethyl)-9-azabicyclo[3.3.1]nonan-3-one oxime

Product 1

HCID 131787589-Benzyl-9-azabicyclo[3.3.1]nonan-3-amineYield 61%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

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.

Workup

  1. filtrationThe mixture was filtered after 24 hours through kieselguhr
  2. customevaporated in vacuo
  3. dissolutionThe resulting oil was dissolved in dilute hydrochloric acid (50 ml)
  4. extractionextracted with ethyl acetate (3×150 ml)
  5. extractionre-extracted with ethyl acetate (3×150 ml)
  6. dry with materialThe combined organic extracts were dried (K2CO3)
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-7194805d1ffb4465b9dd3e84cbe7d409
Source dataset
uspto-grants-1981_06
Patent number
US04273778

Reaction notes

Loading…