3-(N-methyl N-benzylamino)quinuclidine → N-methyl-1-azabicyclo[2.2.2]octan-3-amine
Reaction equation
[CH3:1][N:2]([CH:10]1[CH:15]2[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]2)[CH2:11]1)CC1C=CC=CC=1>[Pd].C(O)C>[CH3:1][NH:2][CH:10]1[CH:15]2[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]2)[CH2:11]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 33.3 g of 3-(N-methyl N-benzylamino)quinuclidine and 16 g of palladium on charcoal at 10% (50% humidity) in 500 ml of ethanol is heated in an autoclave at 80° C. for 6 hours 30 minutes and under a hydrogen pressure of 6 bars. Then it is filtered, the solvent is evaporated (under a good vacuum and when cold) and the residue is distilled (Boiling point [24 mm/Hg]=110° C.). Thus the expected product is obtained with a yield of 43%.
Workup
- filtrationThen it is filtered
- customthe solvent is evaporated (under a good vacuum and when cold) and the residue
- distillationis distilled (Boiling point [24 mm/Hg]=110° C.)
Sources & evidence
- ORD record
- ord-3b80428736fd436a975fcd7ff827a8c7
- Source dataset
- uspto-grants-1987_04
- Patent number
- US04657911
Reaction notes
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