Hydrochloric Acid → HCID 69981064, compound

HRID 2393773Notes

Reaction equation

HRID 2393773 reaction equation
[OH-].[Na+].Cl.N12CCC(CC1)C(=O)C2.C(CC(O)=O)#N.[N:19]12[CH2:26][CH2:25][CH:22]([CH2:23][CH2:24]1)[C:21](=[C:27]([C:31]#[N:32])[C:28]([O-:30])=[O:29])[CH2:20]2.[Na+].Cl>O>[N:19]12[CH2:26][CH2:25][CH:22]([CH2:23][CH2:24]1)[C:21](=[C:27]([C:31]#[N:32])[C:28]([OH:30])=[O:29])[CH2:20]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 9740Cyanoacetic acidHCID 14798Sodium Hydroxide2×HCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)HCID 69981063HCID 69981063, compound

Product 1

HCID 69981064HCID 69981064, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
15 °C

Procedure

40% Aqueous NaOH (370 ml, 3.7 mol) was added to a stirred suspension of 3-quinuclidinone hydrochloride (600 g, 3.7 mol) in water (300 ml) over 30 min while maintaining the temperature at 15°-25° C. The resulting mixture was then cooled to 15° C. and a solution of cyanoacetic acid (380 g, 4.5 mol) in water (150 ml) added in a steady stream over 30 min while stirring and maintaining the temperature at 15°-20° C. After the addition was complete, further 40% aq. NaOH (900 ml, 9.0 mol) was added gradually over 45 min while stirring and maintaining the temperature at 15°-20° C. The resulting reddish solution was then left to stir at ambient temperature for a further 2 h before cooling to 15° C. Seeding with authentic sodium 1-azabicyclo[2.2.2]oct-3-ylidenecyanoacetate induced crystallisation of the same, and the mixture was then chilled further to 7° C. with stirring until a thick slurry of the sodium salt was obtained. After stirring at this temperature for a further 45 min a mixture of conc HCl (725 ml) and water (725 ml) was added in a steady stream over 45 min while stirring and maintaining the temperature at 15°-20° C. After adjusting to pH7 the resulting slurry of the Stage 1 product was stirred at ambient temperature for an additional 45 min before using directly for Stage 2.

Workup

  1. temperaturewhile maintaining the temperature at 15°-25° C
  2. temperaturemaintaining the temperature at 15°-20° C
  3. additionAfter the addition
  4. stirringwhile stirring
  5. temperaturemaintaining the temperature at 15°-20° C
  6. waitThe resulting reddish solution was then left
  7. stirringto stir at ambient temperature for a further 2 h
  8. temperaturebefore cooling to 15° C
  9. customcrystallisation of the same, and the mixture
  10. temperaturewas then chilled further to 7° C.
  11. stirringwith stirring until a thick slurry of the sodium salt
  12. customwas obtained
  13. stirringAfter stirring at this temperature for a further 45 min
  14. additionwas added in a steady stream over 45 min
  15. stirringwhile stirring
  16. temperaturemaintaining the temperature at 15°-20° C
  17. stirringwas stirred at ambient temperature for an additional 45 min

Sources & evidence

ORD record
ord-718ff233c22a489c8ce057fd16ca9096
Source dataset
uspto-grants-1998_09
Patent number
US05808075

Reaction notes

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