Cyclohexanone → 1-Aminocyclohexanecarbonitrile

HRID 1469272Notes

Reaction equation

HRID 1469272 reaction equation
[C-:1]#[N:2].[Na+].[OH-].[NH4+:5].[Cl-].[NH4+].[C:8]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>O>[NH2:5][C:8]1([C:1]#[N:2])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 7967CyclohexanoneHCID 8929Sodium CyanideHCID 14923Ammonium HydroxideHCID 25517Ammonium Chloride

Product 1

HCID 796351-AminocyclohexanecarbonitrileYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Sodium cyanide (23.7 g, 482 mmol) was added to a solution of ammonium hydroxide (28%, 122 mL, 965 mmol) and ammonium chloride (28.4 mL, 531 mmol) in water (100 mL). Cyclohexanone (50 mL, 482 mmol) was added over 5 min. The reaction was heated at 60° C. for 6 h, then was allowed to cool to rt and stir overnight. The mixture was transferred to a separatory funnel and was washed with dichloromethane (3×200 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated under reduced pressure. Purification by flash chromatography (silica gel, eluted with 20% hexanes/ethyl acetate) provided 1-aminocyclohexanecarbonitrile as a clear oil (49.5 g, 83%).

Workup

  1. temperatureto cool to rt
  2. customThe mixture was transferred to a separatory funnel
  3. washwas washed with dichloromethane (3×200 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification
  8. washby flash chromatography (silica gel, eluted with 20% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-98a0a98ed2704a0dbe04c7a2b40f6987
Source dataset
uspto-grants-2015_04
Patent number
US09006264B2

Reaction notes

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