Reaction #1254221

Reaction equation

N-cyclooctyl pyrrolidine

butyl iodide

butyl iodide

potassium bicarbonate

→

N-butyl-N-cyclooctylpyrrolidinium iodide

Yield 90.0%

Solvents

methanol

Conditions

Workup

1. 1
   TemperatureThe reaction mixture is refluxed
2. 2
   workup.STIRRINGthe mixture is stirred
3. 3
   Temperatureat refluxing temperature for an additional 36 hours
4. 4
   ConcentrationThe reaction mixture is concentrated at reduced pressure on a rotary evaporator
5. 5
   Otherto give an off-white colored solid material
6. 6
   WashThe solids are rinsed several times with chloroform
7. 7
   Filtrationfiltered after each rinse
8. 8
   Concentrationconcentrated
9. 9
   Otherto give a white powder whose NMR data
10. 10
    OtherThe reaction affords 109 gm

Procedure

To a solution of 60 gms. (0.33 mole) of N-cyclooctyl pyrrolidine in 600 ml. anhydrous methanol, 150 gm. (0.825 mole) of butyl iodide is added. The reaction mixture is refluxed while stirring for four days. Then an additional equivalent of butyl iodide and one equivalent (33 gm., 0.33 mole) of potassium bicarbonate are added and the mixture is stirred at refluxing temperature for an additional 36 hours. The reaction mixture is concentrated at reduced pressure on a rotary evaporator to give an off-white colored solid material. The solids are rinsed several times with chloroform and filtered after each rinse. All the chloroform rinses are combined and concentrated to give a white powder whose NMR data are acceptable for the desired quaternary ammonium iodide salt. The reaction affords 109 gm. (90% yield) of N-butyl-N-cyclooctylpyrrolidinium iodide. The iodide salt is purified by recrystallization by completely dissolving the iodide salt in acetone, and then precipitating by the addition of ethyl ether to the acetone solution. This procedure gives 98 gms. of white powder with very clean 1H and 13C-NRM spectra.

Source