Реакция #6663

Уравнение реакции

1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-pyrrolidine

ethyl iodide

ethyl iodide

ethyl iodide

→

1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-1-ethyl-pyrrolidinium iodide

Выход 93.0%

Растворители

methanol

Условия реакции

Обработка

1. 1
   Другое(equipped with a mechanical stirrer and a reflux condenser)
2. 2
   Температураthe mixture is heated
3. 3
   Температураat reflux for 3 hours
4. 4
   ТемператураThe reaction mixture is cooled down
5. 5
   Другоеexcess ethyl iodide and the solvent are removed at reduced pressure on a rotary evaporator
6. 6
   ДругоеThe obtained dark tan-colored solids (162 gm) are further purified
7. 7
   workup.DISSOLUTIONby dissolving in acetone (500 ml)
8. 8
   Другоеfollowed by precipitation
9. 9
   workup.ADDITIONby adding diethyl ether
10. 10
    ФильтрацияFiltration
11. 11
    Другоеair-drying the obtained solids

Методика

1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-1-ethyl-pyrrolidinium iodide is prepared from the reaction of the parent amine 1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-pyrrolidine with ethyl iodide. A 100 gm (0.42 mole) of the amine, 1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-pyrrolidine, is dissolved in 1000 ml anhydrous methanol in a 3-litre 3-necked reaction flask (equipped with a mechanical stirrer and a reflux condenser). To this solution, 98 gm (0.62 mole) of ethyl iodide is added, and the mixture is stirred at room temperature for 72 hours. Then, 39 gm (0.25 mol.) of ethyl iodide is added and the mixture is heated at reflux for 3 hours. The reaction mixture is cooled down and excess ethyl iodide and the solvent are removed at reduced pressure on a rotary evaporator. The obtained dark tan-colored solids (162 gm) are further purified by dissolving in acetone (500 ml) followed by precipitation by adding diethyl ether. Filtration and air-drying the obtained solids gives 153 gm (93% yield) of the desired 1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-1-ethyl-pyrrolidinium iodide as a white powder. The product is pure by 1H and 13C-NMR analysis.

Источник