Cyclohexanone → 1-Aminocyclohexanecarbonitrile

HRID 2288294Notes

Reaction equation

HRID 2288294 reaction equation
[C-:1]#[N:2].[Na+].[Cl-].[NH4+:5].[OH-].[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 89.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.23 g of sodium cyanide, 1.58 g of ammonium chloride and 8 ml of ammonium hydroxide are introduced, the whole is taken to 0° C. and 2.1 g of cyclohexanone is added. The reaction medium is left to return to ambient temperature under agitation for 18 hours, diluted in a small amount of water and decanted. The aqueous phase is extracted with methylene chloride, the organic phases are combined, washed with salt water, dried, filtered and concentrated. In this way 2.38 g of expected product (colourless oil) is obtained.

Workup

  1. customis taken to 0° C.
  2. waitThe reaction medium is left
  3. customdecanted
  4. extractionThe aqueous phase is extracted with methylene chloride
  5. washwashed with salt water
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-760aa3e0bcd842e5aa262a391e842d4b
Source dataset
uspto-grants-2000_07
Patent number
US06087509

Reaction notes

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