Cyclohexanone → 1-(Dimethylamino)cyclohexanecarbonitrile

HRID 2071979Notes

Reaction equation

HRID 2071979 reaction equation
[Cl-].[CH3:2][NH2+:3][CH3:4].[C:5]1(=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[C-:12]#[N:13].[K+]>O>[C:12]([C:5]1([N:3]([CH3:4])[CH3:2])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)#[N:13]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 9032Potassium CyanideHCID 12954980Dimethylazanium;chloride

Product 1

HCID 1011881-(Dimethylamino)cyclohexanecarbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Dimethylammonium chloride (81.5 g, 1.0 mole) dissolved in water (150 ml.) was added to cyclohexanone (98.0 g., 1.0 mole), quickly followed by a solution of potassium cyanide (68.0 g, 1.045 mole) in water (150 ml.) added over a period of five minutes. The reaction mixture was stirred for 24 hours during which time a colourless crystalline solid was formed. The solid was filtered off, washed with ice cold water (200 ml.), dissolved in benzene (150 ml.) and rewashed with water (100 ml.). The aqueous layer was extracted with benzene (100 ml.), the benzene solutions then being combined, dried over anhydrous sodium sulphate and evaporated under reduced pressure. The oily residue (144 g.) solidified to give 1-cyanocyclohexyldimethylamine, m.p. 36°.

Workup

  1. additionadded over a period of five minutes
  2. customwas formed
  3. filtrationThe solid was filtered off
  4. washwashed with ice cold water (200 ml.)
  5. dissolutiondissolved in benzene (150 ml.)
  6. extractionThe aqueous layer was extracted with benzene (100 ml.)
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-74a195f831944eb081237e548d88f65f
Source dataset
uspto-grants-1977_09
Patent number
US04049663

Reaction notes

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