HCID 57054725, compound → 3-(8-Methyl-8-azabicyclo[3.2.1]octan-3-yl)aniline

HRID 581222Notes

Reaction equation

HRID 581222 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH:4]=[C:5]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=1)[CH2:6]2>C(O)C>[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1)[CH2:6]2

Participants

3

Reactant 1

HCID 57054725HCID 57054725, compound

Product 1

HCID 572614823-(8-Methyl-8-azabicyclo[3.2.1]octan-3-yl)aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8-Methyl-3-(3-nitrophenyl)-8-azabicyclo[3.2.1]oct-2-ene (D10) (0.146 g, 0.598 mmol) was dissolved in ethanol (25 ml) and was hydrogenated at atmospheric pressure in the presence of 10% PdC (0.1 g) at 50° C. After 2 h, the reaction mixture was allowed to cool to room temp. and hydrogenation was continued for a further 16 h. The reaction mixture was then filtered through kieselguhr and the filter pad was washed with ethanol. The filtrate was then evaporated under reduced pressure to give the title compound as a pale yellow oil, which was dried in vacuo (0.104 g, 81%).

Workup

  1. temperatureto cool to room temp.
  2. waithydrogenation was continued for a further 16 h
  3. filtrationThe reaction mixture was then filtered through kieselguhr
  4. washthe filter pad was washed with ethanol
  5. customThe filtrate was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-8cc0c52f6f9447c69e4fad4b64b8525b
Source dataset
uspto-grants-1999_07
Patent number
US05919932

Reaction notes

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