Acetone → 1-Ethyl-1-azabicyclo[2.2.2]octan-1-ium iodide

HRID 1980563Notes

Reaction equation

HRID 1980563 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[CH2:9]([I:11])[CH3:10].CC(C)=O.C(OCC)C>C(Cl)(Cl)Cl>[I-:11].[CH2:9]([N+:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2)[CH3:10]

Participants

6

Reactant 4

HCID 180AcetoneHCID 3283Diethyl EtherHCID 6340IodoethaneHCID 7527Quinuclidine

Product 1

HCID 136522871-Ethyl-1-azabicyclo[2.2.2]octan-1-ium iodide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

20 grams of Quinuclidine (1 Aza bicyclo [2.2.2] octane, Aldrich) were dissolved in 100 ml of chloroform with stirring and cooling in an ice bath. 28.08 Grams of ethyl iodide (Aldrich) were added dropwise. The mixture became cloudy and was stirred overnight, slowly coming to room temperature. Acetone was added to the solution and then, with stirring, diethyl ether was added dropwise until crystals formed. The filtered solids were washed with acetone and dried under vacuum. The product had the correct microanalysis for C, H, and N.

Workup

  1. temperaturecooling in an ice bath
  2. stirringwas stirred overnight
  3. customslowly coming to room temperature
  4. stirringwith stirring
  5. customformed
  6. washThe filtered solids were washed with acetone
  7. customdried under vacuum

Sources & evidence

ORD record
ord-27153fe7bd144b93a3bb0769607704a8
Source dataset
uspto-grants-1985_04
Patent number
US04510256

Reaction notes

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