Hydrochloric Acid → 1-Piperidinocyclohexanecarbonitrile

HRID 543463Notes

Reaction equation

HRID 543463 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[C:8]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[C-:15]#[N:16].[K+]>O>[N:1]1([C:8]2([C:15]#[N:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7967CyclohexanoneHCID 8082PiperidineHCID 9032Potassium Cyanide

Product 1

HCID 625291-PiperidinocyclohexanecarbonitrileYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Piperidine (44 g, 0.52 mole) was carefully mixed with 45 ml of concentrated HCl and 120 ml of cold water (pH 3-4). To this solution, 50 g (0.52 mole) of cyclohexanone was added, followed by 36 g of KCN in 100 ml of water with vigorous stirring. The resulting solution was allowed to stir at room temperature for overnight. After 2 hours, a white precipitate was formed. The crystalline precipitate was collected by filtration and washed with cold water. Recrystallization from 95% ethanol (300 ml) gave 88 g of white crystalline solid, mp 66°-8° C., in 88% yield.

Workup

  1. waitAfter 2 hours
  2. customa white precipitate was formed
  3. filtrationThe crystalline precipitate was collected by filtration
  4. washwashed with cold water
  5. customRecrystallization from 95% ethanol (300 ml)

Sources & evidence

ORD record
ord-38a0ed76d6034134be859d196b5181bc
Source dataset
uspto-grants-1984_05
Patent number
US04446065

Reaction notes

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