Reaktion #169608

Reaktionsgleichung

3-pyridinecarboxaldehyde

Potassium hydroxide

3-Quinuclidinone hydrochloride

→

2-((3-pyridinyl)methylene)-1-azabicyclo[2.2.2]octan-3-one

Ausbeute 89.3%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeequipped with a mechanical stirrer
2. 2
   Sonstigeresulting in a rise in reaction temperature from 50° C. to 56° C
3. 3
   SonstigeUpon completion of the reaction
4. 4
   Filtrationthe reaction mixture was filtered through a sintered glass funnel
5. 5
   Waschenthe filter cake was washed with methanol (74.2 L)
6. 6
   EinengenThe filtrate was concentrated
7. 7
   Sonstigetransferred to a reaction flask
8. 8
   workup.ADDITIONwater (66.0 L) was added
9. 9
   workup.STIRRINGThe suspension was stirred for a minimum of 30 min
10. 10
    Filtrationfiltered
11. 11
    Waschenthe filter cake was washed with water (90.0 L) until the pH of the rinse
12. 12
    SonstigeThe solid was dried under vacuum at 50° C.±5° C. for a minimum of 12 h

Vorschrift

3-Quinuclidinone hydrochloride (8.25 kg, 51.0 mol) and methanol (49.5 L) were added to a 100 L glass reaction flask, under an nitrogen atmosphere, equipped with a mechanical stirrer, temperature probe, and condenser. Potassium hydroxide (5.55 kg, 99.0 mol) was added via a powder funnel over an approximately 30 min period, resulting in a rise in reaction temperature from 50° C. to 56° C. Over an approximately 2 h period, 3-pyridinecarboxaldehyde (4.80 kg, 44.9 mol) was added to the reaction mixture. The resulting mixture was stirred at 20° C.±5° C. for a minimum of 12 h, as the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was filtered through a sintered glass funnel and the filter cake was washed with methanol (74.2 L). The filtrate was concentrated, transferred to a reaction flask, and water (66.0 L) was added. The suspension was stirred for a minimum of 30 min, filtered, and the filter cake was washed with water (90.0 L) until the pH of the rinse was 7-9. The solid was dried under vacuum at 50° C.±5° C. for a minimum of 12 h to give 8.58 kg (89.3%) of 2-((3-pyridinyl)methylene)-1-azabicyclo[2.2.2]octan-3-one.

Quelle