反応 #74952

反応方程式

chloromethyl methylthioether

chloromethylmethylthioether

N-(2-chloro-benzyl)-2-(2-thienyl)ethylamine

water

→

5-(2-chloro-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine hydrochloride

収率 142.2%

溶媒

dimethylsulfoxide

反応条件

後処理

1. 1
   workup.ADDITIONare added, over 30 minutes
2. 2
   温度The temperature of the reaction medium increases gradually
3. 3
   温度it is maintained at 80°-85° C, throughout the addition step
4. 4
   温度the medium is cooled to 6° C
5. 5
   その他The desired product precipitates out readily
6. 6
   ろ過After filtration
7. 7
   洗浄washing with 2×70 ml acetone, there

実験手順

To 52 g (0.2 M) N-(2-chloro-benzyl)-2-(2-thienyl)ethylamine dissolved in 60 ml dimethylsulfoxide and heated at 60° C. are added, over 30 minutes, 51 g (0.3 M) crude chloromethylmethylthioether prepared in step (a) above. The temperature of the reaction medium increases gradually and it is maintained at 80°-85° C, throughout the addition step, by cooling with water. When addition of chloromethyl methylthioether is completed, the medium is cooled to 6° C. The desired product precipitates out readily. After filtration and washing with 2×70 ml acetone, there are obtained 44.1 g 5-(2-chloro-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine hydrochloride (Yield: 73.5%). Treatment of the filtrates provides another 10 g of the desired product (Yield: 90% M.p.=190° C.). The resulting crude product contains 1-2% impurities and may be made analytically pure by recrystallization from ethanol.

出典