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

HRID 542441Notes

Reaction equation

HRID 542441 reaction equation
[NH2:1][CH:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.[CH:10](=O)C1C=CC=CC=1.O>C1(C)C=CC=CC=1>[CH3:10][NH:1][CH:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 962WaterHCID 1232383-Aminoquinuclidine

Product 1

HCID 19775384N-methyl-1-azabicyclo[2.2.2]octan-3-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

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.

Workup

  1. temperatureto reflux for 45 minutes
  2. customformed
  3. customThen the solvent is evaporated
  4. dissolutionthe residue is dissolved in 800 ml of methanol
  5. addition15 g of potassium borohydride are added within 3 hours
  6. customThen the solvent is evaporated
  7. customthe mixture obtained
  8. extractionis extracted with ethyl acetate (or with chloroform)
  9. dry with materialdried on sodium (or magnesium) sulfate
  10. filtrationfiltered
  11. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-c7711031d00b4fadb2b7e24aed5151c1
Source dataset
uspto-grants-1987_04
Patent number
US04657911

Reaction notes

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