N-methyl-1-azabicyclo[2.2.2]octan-3-amine

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

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%. 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.)

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 73.7 g of 3-benzylamino quinuclidine in water (≃300 to 400 ml) are added, while cooling to 5° C., 51 ml of a 40% aqueous formaldehyde solution. Then after the addition, the mixture is left for 30 minutes at 5° C., then 32 g of sodium cyanoborohydride are added within 1 to 2 hours. Then it is left at room temperature for 12 hours, extracted with ethyl acetate, the mixture obtained is dried on sodium (or magnesium) sulfate, filtered, the filtrate is evaporated and the residue is distilled (Boiling point [0.04 mm/Hg]=125° C.). Thus the expected product is obtained practically quantitatively. Then after the addition Then it is left at room temperature for 12 hours extracted with ethyl acetate the mixture obtained is dried on sodium (or magnesium) sulfate filtered the filtrate is evaporated the residue is distilled (Boiling point [0.04 mm/Hg]=125° C.)

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 73.7 g of 3-benzylamino quinuclidine in water (≃300 to 400 ml) are added, while cooling to 5° C., 51 ml of a 40% aqueous formaldehyde solution. Then after the addition, the mixture is left for 30 minutes at 5° C., then 32 g of sodium cyanoborohydride are added within 1 to 2 hours. Then it is left at room temperature for 12 hours, extracted with ethyl acetate, the mixture obtained is dried on sodium (or magnesium) sulfate, filtered, the filtrate is evaporated and the residue is distilled (Boiling point [0.04 mm/Hg]=125° C.). Thus the expected product is obtained practically quantitatively. Then after the addition Then it is left at room temperature for 12 hours extracted with ethyl acetate the mixture obtained is dried on sodium (or magnesium) sulfate filtered the filtrate is evaporated the residue is distilled (Boiling point [0.04 mm/Hg]=125° C.)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 50 g of 3-amino quinuclidine and 40 ml of benzaldehyde in 1000 ml of toluene is brought to reflux for 45 minutes, while eliminating the water formed. Then the solvent is evaporated, the residue is dissolved in 800 ml of methanol and 15 g of potassium borohydride are added within 3 hours while maintaining the temperature at 0° C. Then the solvent is evaporated, the residue is taken up in water, the mixture obtained is extracted with ethyl acetate (or with chloroform), dried on sodium (or magnesium) sulfate, filtered and the filtrate is evaporated. Thus 85 g (yield ≃100%) of the pure expected product are obtained (one spot in TLC) which is in liquid form. to reflux for 45 minutes formed Then the solvent is evaporated the residue is dissolved in 800 ml of methanol 15 g of potassium borohydride are added within 3 hours Then the solvent is evaporated the mixture obtained is extracted with ethyl acetate (or with chloroform) dried on sodium (or magnesium) sulfate filtered the filtrate is evaporated

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

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%. 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.)

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 73.7 g of 3-benzylamino quinuclidine in water (≃300 to 400 ml) are added, while cooling to 5° C., 51 ml of a 40% aqueous formaldehyde solution. Then after the addition, the mixture is left for 30 minutes at 5° C., then 32 g of sodium cyanoborohydride are added within 1 to 2 hours. Then it is left at room temperature for 12 hours, extracted with ethyl acetate, the mixture obtained is dried on sodium (or magnesium) sulfate, filtered, the filtrate is evaporated and the residue is distilled (Boiling point [0.04 mm/Hg]=125° C.). Thus the expected product is obtained practically quantitatively. Then after the addition Then it is left at room temperature for 12 hours extracted with ethyl acetate the mixture obtained is dried on sodium (or magnesium) sulfate filtered the filtrate is evaporated the residue is distilled (Boiling point [0.04 mm/Hg]=125° C.)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 50 g of 3-amino quinuclidine and 40 ml of benzaldehyde in 1000 ml of toluene is brought to reflux for 45 minutes, while eliminating the water formed. Then the solvent is evaporated, the residue is dissolved in 800 ml of methanol and 15 g of potassium borohydride are added within 3 hours while maintaining the temperature at 0° C. Then the solvent is evaporated, the residue is taken up in water, the mixture obtained is extracted with ethyl acetate (or with chloroform), dried on sodium (or magnesium) sulfate, filtered and the filtrate is evaporated. Thus 85 g (yield ≃100%) of the pure expected product are obtained (one spot in TLC) which is in liquid form. to reflux for 45 minutes formed Then the solvent is evaporated the residue is dissolved in 800 ml of methanol 15 g of potassium borohydride are added within 3 hours Then the solvent is evaporated the mixture obtained is extracted with ethyl acetate (or with chloroform) dried on sodium (or magnesium) sulfate filtered the filtrate is evaporated