Reaktion #3858

Reaktionsgleichung

2-propoxybenzoyl chloride

3-amino quinuclidine dihydrochloride

barium hydroxide octahydrate

→

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-propoxybenzamide, hydrochloride

Lösungsmittel

methylene chloride

carbon dioxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was warmed for 5 minutes
2. 2
   Sonstigedried to a powder on a rotary evaporator
3. 3
   Extraktionthe powder was extracted in sequence with hot benzene
4. 4
   workup.ADDITIONa 1:1 mixture of benzene-methylene chloride solution
5. 5
   TrocknenThe combined extracts were dried over magnesium sulfate
6. 6
   Filtrationthe mixture filtered
7. 7
   TemperaturThe mixture was warmed on a steam bath
8. 8
   Sonstigeto evaporate about 75% of the methylene chloride
9. 9
   workup.ADDITIONLigroin (60-110) was added
10. 10
    SonstigeThe solid was recrystallized from anhydrous ethyl alcohol
11. 11
    Sonstigeto give 3.9 g (62.0%), m.p. 210°-211° C.

Vorschrift

To a solution of 3.82 g (0.0192 mole) of 3-amino quinuclidine dihydrochloride in about 25 ml of carbon dioxide-free water was added 8 g (0.025 mole) of barium hydroxide octahydrate. The mixture was warmed for 5 minutes and then dried to a powder on a rotary evaporator. While protecting from contamination with carbon dioxide in the atmosphere, the powder was extracted in sequence with hot benzene and a 1:1 mixture of benzene-methylene chloride solution. The combined extracts were dried over magnesium sulfate and the mixture filtered. To the filtrate with agitation was added dropwise a solution of 3.4 g (0.0171 mole) of 2-propoxybenzoyl chloride in 50 ml of methylene chloride. The mixture was warmed on a steam bath to evaporate about 75% of the methylene chloride. Ligroin (60-110) was added and the mixture solidified. The solid was recrystallized from anhydrous ethyl alcohol to give 3.9 g (62.0%), m.p. 210°-211° C.

Quelle