Ammonium Acetate → 9-Methyl-9-azabicyclo(3.3.1)nonan-3-amine

HRID 1680432Notes

Reaction equation

HRID 1680432 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH:3]1[CH2:4][C:5](=[N:11]O)[CH2:6]2.C([O-])(=O)C.[NH4+]>C(O)C.[Ni]>[NH2:11][CH:5]1[CH2:4][CH:3]2[N:2]([CH3:1])[CH:7]([CH2:8][CH2:9][CH2:10]2)[CH2:6]1

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 32191339-Methyl-9-azabicyclo[3.3.1]nonan-3-one oxime

Product 1

HCID 144031759-Methyl-9-azabicyclo(3.3.1)nonan-3-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

N-methyl-9-azabicyclo-[3.3.1]-nonan-3-one oxime (3.25 g., 0.02 mole) was dissolved in ethanol and hydrogenated over Raney nickel in the presence of ammonium acetate at 300 p.s.i. at 50° C. for 24 hours. The mixture was filtered, evaporated in vacuo, dissolved in dilute hydrochloric acid, basified and extracted into ethyl acetate. The combined organic layers were dried (K2CO3), filtered and evaporated in vacuo to yield 3-amino-9-methyl-9-azabicyclo-3.3.1]-nonane (2.67 g., 90%), used without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated in vacuo
  3. dissolutiondissolved in dilute hydrochloric acid
  4. extractionextracted into ethyl acetate
  5. dry with materialThe combined organic layers were dried (K2CO3)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto yield 3-amino-9-methyl-9-azabicyclo-3
  9. custom3.1]-nonane (2.67 g., 90%), used without further purification

Sources & evidence

ORD record
ord-61618493a8a7484bbca354fa44955cea
Source dataset
uspto-grants-1981_06
Patent number
US04273778

Reaction notes

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