Sodium Cyanide → 2-{1-Azabicyclo[2.2.2]octan-4-yl}acetonitrile

HRID 1923408Notes

Reaction equation

HRID 1923408 reaction equation
[N:1]12[CH2:8][CH2:7][C:4]([CH2:9]O)([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.S([O-])(=O)(=O)C.CS(Cl)(=O)=O.[C-:21]#[N:22].[Na+]>C(Cl)(Cl)Cl.CN(C)C=O.C(N(CC)CC)C>[N:1]12[CH2:8][CH2:7][C:4]([CH2:9][C:21]#[N:22])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2

Participants

8

Reactant 4

HCID 8929Sodium CyanideHCID 31297Methanesulfonyl chlorideHCID 85257Methanesulfonate2×HCID 1413111-Azabicyclo(2.2.2)octane-4-methanol

Product 1

HCID 220566352-{1-Azabicyclo[2.2.2]octan-4-yl}acetonitrileYield 72%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Quinuclidin-4-ylmethanol (1.94 g, 0.014 moles) was converted to the corresponding mesylate by treatment with methane sulphonyl chloride and triethylamine in chloroform. The mesylate was dissolved in dimethylformamide (50 ml) and treated with sodium cyanide (1.4 g, 0.028 moles) at 120° C. for 18 hours. The mixture was cooled and concentrated in vacuo. The residue was partitioned between saturated potassium carbonate and chloroform. The organic layer was separated and dried (Na2SO4), filtered and evaporated to dryness. Chromatography on silica gel eluting with 0-10% methanol/chloroform gave the title compound 1.5 g (72%). M.S. (+ve electrospray) m/z 151 (MH+, 100%).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between saturated potassium carbonate and chloroform
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-f9fa8c0d47a04ce6aec068dc333378d9
Source dataset
uspto-grants-2012_05
Patent number
USRE043390E1

Reaction notes

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