Reaction #1350564

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 was refluxed
2. 2
   workup.STIRRINGthe mixture was stirred
3. 3
   Temperatureat refluxing temperature for an additional 36 hours
4. 4
   ConcentrationThe reaction mixture was concentrated at reduced pressure on a rotary evaporator
5. 5
   Otherto give an off-white colored solid material
6. 6
   WashThe solids were 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 afforded 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 was added. The reaction mixture was refluxed while stirring for four days. Then an additional equivalent of butyl iodide and one equivalent (33 gm., 0.33 mole) of potassium bicarbonate were added and the mixture was stirred at refluxing temperature for an additional 36 hours. The reaction mixture was concentrated at reduced pressure on a rotary evaporator to give an off-white colored solid material. The solids were rinsed several times with chloroform and filtered after each rinse. All the chloroform rinses were combined and concentrated to give a white powder whose NMR data were acceptable for the desired quaternary ammonium iodide salt. The reaction afforded 109 gm. (90% yield) of N-butyl-N-cyclooctylpyrrolidinium iodide. The iodide salt was 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 gave 98 gms. of white powder with very clean 1H and 13C-NRM spectra.

Source