Sodium Cyanide → 3-Hydroxyquinuclidine-3-carbonitrile

HRID 1650877Notes

Reaction equation

HRID 1650877 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:10])[CH2:3]2.[C-:11]#[N:12].[Na+]>O>[C:11]([C:4]1([OH:10])[CH:5]2[CH2:8][CH2:9][N:2]([CH2:7][CH2:6]2)[CH2:3]1)#[N:12]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)

Product 1

HCID 2972833-Hydroxyquinuclidine-3-carbonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1,420 g (8.78 mole) of quinuclidine-3-one-hydrochloride were dissolved in 1800 ml of cold water and at 15° C., 432 g (8.81 mole) of sodium cyanide and 1600 of ml water were added dropwise over one hour followed by stirring for another hour at this temperature. The mixture was filtered, washed with cold water, and dried at 60° C. to obtain 1,290 g (8.48 mole) of 3-cyano-3-hydroxy-quinuclidine (97% yield), in the form of white crystals having a melting point of 157° to 159° C.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with cold water
  3. customdried at 60° C.

Sources & evidence

ORD record
ord-2c7fe0a53c7a4fbbb454e5a1f48c0de8
Source dataset
uspto-grants-1990_05
Patent number
US04925942

Reaction notes

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