Potassium Cyanide → 1-Azabicyclo(2.2.2)octane-3-carbonitrile

HRID 2293433Notes

Reaction equation

HRID 2293433 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C:2]2=O.C(C1C=C(C(C)C)C=C(C(C)C)C=1S(NN)(=O)=O)(C)C.[C-:30]#[N:31].[K+]>CO>[C:30]([CH:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1)#[N:31]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 3593332,4,6-TriisopropylbenzenesulphonohydrazideHCID 5661191-azabicyclo[2.2.2]octan-2-one

Product 1

HCID 1428651-Azabicyclo(2.2.2)octane-3-carbonitrileYield 23.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Quinuclidinone (24.2 g, 0.19 mol) and 2,4,6-triisopropylbenzene sulphonohydrazide (72 g, 0.24 mol) (250 ml) were stirred together in anhydrous methanol for 3 hours. Potassium cyanide (33.8 g, 0.51 mol) was added and the mixture heated under reflux for 5 hours. The material isolated, after evaporation of the solvent, was partitioned between water and dichloromethane. The organic phase was dried (sodium sulphate) and evaporated and the residue fractionally distilled under reduced pressure to give 3-cyano-quinuclidine (6.1 g), approximate b.p. 95°-100° at 13 N.m-2 (0.1 mmHg).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 5 hours
  3. customThe material isolated
  4. customafter evaporation of the solvent
  5. customwas partitioned between water and dichloromethane
  6. dry with materialThe organic phase was dried (sodium sulphate)
  7. customevaporated
  8. distillationthe residue fractionally distilled under reduced pressure

Sources & evidence

ORD record
ord-5335a9bcb1f848ca8d0d18f13ff919c3
Source dataset
uspto-grants-1997_11
Patent number
US05686463

Reaction notes

Loading…