Reaction #6663

Reaction equation

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

ethyl iodide

ethyl iodide

ethyl iodide

→

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

Yield 93.0%

Solvents

methanol

Conditions

Workup

1. 1
   Other(equipped with a mechanical stirrer and a reflux condenser)
2. 2
   Temperaturethe mixture is heated
3. 3
   Temperatureat reflux for 3 hours
4. 4
   TemperatureThe reaction mixture is cooled down
5. 5
   Otherexcess ethyl iodide and the solvent are removed at reduced pressure on a rotary evaporator
6. 6
   OtherThe obtained dark tan-colored solids (162 gm) are further purified
7. 7
   workup.DISSOLUTIONby dissolving in acetone (500 ml)
8. 8
   Otherfollowed by precipitation
9. 9
   workup.ADDITIONby adding diethyl ether
10. 10
    FiltrationFiltration
11. 11
    Otherair-drying the obtained solids

Procedure

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.

Source