Potassium Cyanide → 4-Cyano-4-(piperidin-1-yl)cyclohexyl benzoate

HRID 543461Notes

Reaction equation

HRID 543461 reaction equation
[C:1]([O:9][CH:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[C-:24]#[N:25].[K+]>C(O)C.O>[C:1]([O:9][CH:10]1[CH2:15][CH2:14][C:13]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)([C:24]#[N:25])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 2426774-(Benzoyloxy)cyclohexanoneHCID 2723721Piperidine, hydrochloride (1:1)

Product 1

HCID 133067554-Cyano-4-(piperidin-1-yl)cyclohexyl benzoateYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-Benzoyloxycyclohexanone (13.5 g, 62 mmoles), piperidine hydrochloride (8.1 g, 67 mmoles) and potassium cyanide (4.25 g, 65 mmoles) were dissolved in 60 ml of 95% ethanol and 60 ml of water. The mixture was stirred at room temperature for 16 hours (overnight). The resulting solid material was collected by filtration. The filtrate was diluted with 100 ml of water and the solution was extracted with ether. Concentration of the ethereal solution gave more solid material. The combined solid material was recrystallized from 90% ethanol to give 14.5 g of white crystalline solid (mp: 165°-171° C.) in 75% yield.

Workup

  1. filtrationThe resulting solid material was collected by filtration
  2. additionThe filtrate was diluted with 100 ml of water
  3. extractionthe solution was extracted with ether
  4. customConcentration of the ethereal solution gave more solid material
  5. customThe combined solid material was recrystallized from 90% ethanol

Sources & evidence

ORD record
ord-3f2b1cd117874e938a46920dd877daa0
Source dataset
uspto-grants-1984_05
Patent number
US04446065

Reaction notes

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