Potassium Cyanide → 3-Hydroxyquinuclidine-3-carbonitrile

HRID 1248652Notes

Reaction equation

HRID 1248652 reaction equation
[C-:1]#[N:2].[K+].Cl.[N:5]12[CH2:12][CH2:11][CH:8]([CH2:9][CH2:10]1)[C:7](=[O:13])[CH2:6]2>O>[C:1]([C:7]1([OH:13])[CH:8]2[CH2:11][CH2:12][N:5]([CH2:10][CH2:9]2)[CH2:6]1)#[N:2]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)

Product 1

HCID 2972833-Hydroxyquinuclidine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of potassium cyanide (10.15 g, 0.156 mol) in water (31.25 ml) was added dropwise to a solution of 1-azabicyclo[2.2.2]octan-3-one hydrochloride (25.0 g, 0.155 mol) in water (31.25 ml) at 0°-5°. Following the addition, the reaction mixture was stirred for 3 h and then filtered. The solid was washed with ice-cold water (2×15 ml) and was then dried over phosphorus pentoxide overnight, m.p. 155°-156°. Recrystallisation of a 1 g sample from dioxane gave pure 3-cyano-3-hydroxy-1-azabicyclo[2.2.2]octane, m.p. 172°-173°.

Workup

  1. additionthe addition
  2. filtrationfiltered
  3. washThe solid was washed with ice-cold water (2×15 ml)
  4. dry with materialwas then dried over phosphorus pentoxide overnight, m.p. 155°-156°
  5. customRecrystallisation of a 1 g sample from dioxane

Sources & evidence

ORD record
ord-c43c68adcadc4cc983911767d5daae53
Source dataset
uspto-grants-1985_06
Patent number
US04525475

Reaction notes

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