Methanol → 4-Benzyl-1-cyano-1-(dimethylamino)cyclohexane hydrochloride

HRID 67691Notes

Reaction equation

HRID 67691 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:15]#[N:16].[K+].[ClH:18].[CH3:19][NH:20][CH3:21].CO>CNC>[ClH:18].[CH2:1]([CH:8]1[CH2:13][CH2:12][C:11]([C:15]#[N:16])([N:20]([CH3:21])[CH3:19])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 9032Potassium CyanideHCID 10473Dimethylamine, hydrochlorideHCID 106552354-Benzylcyclohexanone

Product 1

HCID 205276224-Benzyl-1-cyano-1-(dimethylamino)cyclohexane hydrochlorideYield 61%

Reagents, catalysts & solvents 1

HCID 674DimethylamineSolvent

Procedure

A mixture of 4-benzylcyclohexanone (4.40 g, 0.023 mole), 3.67 g of potassium cyanide, 5.50 g of dimethylamine hydrochloride and 3 ml of methanol in 30 ml of saturated aqueous dimethylamine was stirred at room temperature for 3 days. The mixture was then extracted thoroughly with CH2Cl2, and the organic layer was concentrated in vacuo. The residue was dissolved in diethyl ether, and the basic material was precipitated with 2 N HCl in diethyl ether. This solid was recrystallized from methylene chloride:ethyl acetate to give 3.91 g (61%) of 4-benzyl-1-cyano-1-(dimethylamino)cyclohexane hydrochloride, m.p. 150°-154° C.

Workup

  1. extractionThe mixture was then extracted thoroughly with CH2Cl2
  2. concentrationthe organic layer was concentrated in vacuo
  3. dissolutionThe residue was dissolved in diethyl ether
  4. customthe basic material was precipitated with 2 N HCl in diethyl ether
  5. customThis solid was recrystallized from methylene chloride

Sources & evidence

ORD record
ord-91332c9baf844cce9d20ab1fc2573449
Source dataset
uspto-grants-1982_08
Patent number
US04346101

Reaction notes

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