Acetone Cyanohydrin → 1-Benzyl-4-hydroxypiperidine-4-carbonitrile

HRID 271615Notes

Reaction equation

HRID 271615 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC(C)(C)[C:17]#[N:18].C([O-])([O-])=O.[K+].[K+]>C(O)C.C(OCC)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([OH:14])([C:17]#[N:18])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6406Acetone CyanohydrinHCID 11430Potassium CarbonateHCID 192201-Benzyl-4-piperidone

Product 1

HCID 801891-Benzyl-4-hydroxypiperidine-4-carbonitrileYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2 g (10.6 mmoles) of 1-benzyl-piperidin-4-one in 14 ml of ethanol are added 6.8 ml (74.5 mmoles) of 2-hydroxy-2-methyl-propionitrile and 0.41 g (3 mmoles) of K2CO3 at 0° C. The mixture is stirred at 0° C. for 5 hours and diluted with diethyl ether. The organic layer is washed with water, dried over Na2SO4 and concentrated. Chromatography on silica gel (CH2Cl2:MeOH=9:1) gives 1.94 g of desired 1-benzyl-4-hydroxy-piperidine-4-carbonitrile in 85% yield.

Workup

  1. washThe organic layer is washed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-117598fd5eed4d3a90bc3d5247439621
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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