Reaktion #74952

Reaktionsgleichung

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

Ausbeute 142.2%

Lösungsmittel

dimethylsulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONare added, over 30 minutes
2. 2
   TemperaturThe temperature of the reaction medium increases gradually
3. 3
   Temperaturit is maintained at 80°-85° C, throughout the addition step
4. 4
   Temperaturthe medium is cooled to 6° C
5. 5
   SonstigeThe desired product precipitates out readily
6. 6
   FiltrationAfter filtration
7. 7
   Waschenwashing with 2×70 ml acetone, there

Vorschrift

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.

Quelle