Hydrochloric Acid → 1-Benzyl-4-hydroxypiperidine-4-carbonitrile

HRID 2407748Notes

Reaction equation

HRID 2407748 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.[C-:15]#[N:16].[K+].Cl>C(OCC)C.O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([OH:14])([C:15]#[N:16])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 192201-Benzyl-4-piperidone

Product 1

HCID 801891-Benzyl-4-hydroxypiperidine-4-carbonitrileYield 51%

Reagents, catalysts & solvents 1

HCID 21584184Diethylether waterSolvent

Procedure

A solution of 1-benzylpiperidin-4-one (7.00 g) in 1:1 diethyl ether-water (30 mL) was cooled to 0° C. and treated with potassium cyanide (6.02 g), followed by hydrochloric acid (7.71 mL). The ice bath was removed and the mixture was stirred at room temperature for 18 hours. The phases were separated, and the aqueous layer was extracted with diethyl ether, dried and evaporated in vacuo to provide the title compound (4.08 g) having the following physical data.

Workup

  1. customThe ice bath was removed
  2. customThe phases were separated
  3. extractionthe aqueous layer was extracted with diethyl ether
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-e0550adfb4ad49d1841b0c6485e7b5bf
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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