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

HRID 1641001Notes

Reaction equation

HRID 1641001 reaction equation
[N:1]12[CH2:8][CH2:7][C:4]([CH2:9][C:10](Cl)=O)([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[N:13]12CCC(CO)(CC1)CC2.S([O-])(=O)(=O)C.[C-]#N.[Na+]>CN(C)C=O>[N:1]12[CH2:8][CH2:7][C:4]([CH2:9][C:10]#[N:13])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2

Participants

6

Reactant 4

HCID 8929Sodium CyanideHCID 85257MethanesulfonateHCID 1413111-Azabicyclo(2.2.2)octane-4-methanolHCID 220566712-(Quinuclidin-4-yl)acetyl chloride

Product 1

HCID 220566352-{1-Azabicyclo[2.2.2]octan-4-yl}acetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(Quinuclidin-4-yl)acetyl chloride may be made by converting (quinuclidin-4-yl)methanol (vide supra) to the mesylate (methanesulfonylchloride/triethylamine in chloroform) which is then treated with sodium cyanide in dimethylformamide to form (quinuclidin-4-yl)acetonitrile. Heating this in ethanol saturated with hydrogen chloride gas produces the corresponding ethyl ester which is hydrolyzed to the acid by treatment with 6N hydrochloric acid. Finally, the acid is converted to the acid chloride as described above.

Sources & evidence

ORD record
ord-34d811726af34d329b91396f5db0e73a
Source dataset
uspto-grants-2012_02
Patent number
US08114891B2

Reaction notes

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