Sodium Cyanide → 3-Hydroxyquinuclidine-3-carbonitrile

HRID 2165535Notes

Reaction equation

HRID 2165535 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 99.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a cooled (ice bath), stirred solution of 3-quinuclidinone hydrochloride (300 g) in water (400 ml) was added dropwise a solution of sodium cyanide (90.97 g) in water (400 ml). After stirring at ice bath temperature for three hours the precipitate was collected by filtration, washed with water and dried under vacuum to afford the title compound (282 g); m.p. 153°-157° C. (lit m.p. 152°-155° C.; Helv. Chim. Acta., 1954, 37, 1689).

Workup

  1. temperatureTo a cooled (ice bath)
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-59ca216226734555832d27ea6b70fa49
Source dataset
uspto-grants-1990_07
Patent number
US04940703

Reaction notes

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