反応 #3857

反応方程式

3-aminoquinuclidine dihydrochloride

2,4-dimethoxybenzoyl chloride

sodium carbonate

water

→

white solid

収率 23.7%

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

収率 23.7%

溶媒

chloroform

反応条件

後処理

1. 1
   workup.ADDITIONto achieve good mixing of the 2 layers for 20 hrs
2. 2
   その他The chloroform layer was then separated
3. 3
   洗浄washed with water
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   濃縮concentrated to an impure oil
6. 6
   その他The oil was triturated twice with 20 ml portions of petroleum ether
7. 7
   その他to remove some impurities
8. 8
   workup.DISSOLUTIONThe oil was then dissolved in diethyl ether
9. 9
   ろ過filtered
10. 10
    その他to remove a small amount of insoluble material
11. 11
    workup.ADDITIONThe filtrate was treated with ethereal hydrogen chloride
12. 12
    その他the resulting salt collected

実験手順

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.

出典