Reaktion #3857

Reaktionsgleichung

3-aminoquinuclidine dihydrochloride

2,4-dimethoxybenzoyl chloride

sodium carbonate

water

→

white solid

Ausbeute 23.7%

N-(1-Azabicyclo[2.2.2]oct-3-yl)-2,4-dimethoxybenzamide, hydrochloride

Ausbeute 23.7%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONto achieve good mixing of the 2 layers for 20 hrs
2. 2
   SonstigeThe chloroform layer was then separated
3. 3
   Waschenwashed with water
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Einengenconcentrated to an impure oil
6. 6
   SonstigeThe oil was triturated twice with 20 ml portions of petroleum ether
7. 7
   Sonstigeto remove some impurities
8. 8
   workup.DISSOLUTIONThe oil was then dissolved in diethyl ether
9. 9
   Filtrationfiltered
10. 10
    Sonstigeto remove a small amount of insoluble material
11. 11
    workup.ADDITIONThe filtrate was treated with ethereal hydrogen chloride
12. 12
    Sonstigethe resulting salt collected

Vorschrift

A mixture of 3-aminoquinuclidine dihydrochloride, 6.95 g, (0.349), 2,4-dimethoxybenzoyl chloride, 700 g, (0.0349 mole), anhydrous sodium carbonate, 36.99 g, (0.349 mole), 175 ml water, and 175 ml chloroform was stirred rapidly to achieve good mixing of the 2 layers for 20 hrs. The chloroform layer was then separated, washed with water, dried over anhydrous magnesium sulfate, and concentrated to an impure oil. The oil was triturated twice with 20 ml portions of petroleum ether to remove some impurities. The oil was then dissolved in diethyl ether and filtered to remove a small amount of insoluble material. The filtrate was treated with ethereal hydrogen chloride and the resulting salt collected to yield 2.70 g (23.7% yield) white solid. The salt was recrystallized from ethanol-isopropyl ether. Further recrystallization from methanol-ethyl ether yielded a white solid, m.p. 211°-212° C. The NMR analysis was satisfactory.

Quelle