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

HRID 280479

Reaction equation

HRID 280479 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-18eefcdd3d8042688da2c968be430e09
Source dataset
uspto-grants-1986_05
Patent number
US04589977

Linked notes

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