Butyl iodide → HCID 22995133, compound

HRID 1167039Notes

Reaction equation

HRID 1167039 reaction equation
[CH:1]1([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:14]([I:18])[CH2:15][CH2:16][CH3:17].C(=O)(O)[O-].[K+]>CO>[I-:18].[CH2:14]([N+:9]1([CH:1]2[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:13][CH2:12][CH2:11][CH2:10]1)[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 10962Butyl iodide2×HCID 516893Potassium BicarbonateHCID 232778741-Cyclooctylpyrrolidine

Product 1

HCID 22995133HCID 22995133, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. temperatureThe reaction mixture is refluxed
  2. stirringthe mixture is stirred
  3. temperatureat refluxing temperature for an additional 36 hours
  4. concentrationThe reaction mixture is concentrated at reduced pressure on a rotary evaporator
  5. customto give an off-white colored solid material
  6. washThe solids are rinsed several times with chloroform
  7. filtrationfiltered after each rinse
  8. concentrationconcentrated
  9. customto give a white powder whose NMR data
  10. customThe reaction affords 109 gm

Sources & evidence

ORD record
ord-d50a1a46a7c4468a81adef363acedd4c
Source dataset
uspto-grants-2003_09
Patent number
US06616911B2

Reaction notes

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