Hydrochloric Acid → 1,4-Bis-dimethylamino-4-phenylcyclohexane carbonitrile

HRID 76916Notes

Reaction equation

HRID 76916 reaction equation
[CH3:1][NH:2][CH3:3].[CH3:4][N:5]([CH3:19])[C:6]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]1.[C-:20]#[N:21].[K+].Cl>O.CO>[CH3:1][N:2]([CH3:3])[C:9]1([C:20]#[N:21])[CH2:10][CH2:11][C:6]([N:5]([CH3:19])[CH3:4])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 9032Potassium CyanideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 683066961,4-Bis-dimethylamino-4-phenylcyclohexane carbonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

40% aqueous dimethylamine solution (14 mL, 110.5 mmol), 4-dimethylamino-4-phenylcyclohexanone (5.00 g, 23.04 mmol) and potassium cyanide (3.60 g, 55.3 mmol) were added to a mixture of 4N hydrochloric acid (14 mL) and methanol (5 mL) with ice cooling. The mixture was stirred for 2 d at room temperature and then after adding water (200 mL) was extracted with ether (4×150 mL). After the solution was concentrated to low volume, the residue was taken up in dichloromethane (200 mL) and dried with magnesium sulphate overnight, filtered and the solvent removed in a vacuum. The nitrile was obtained as an oil which was crystallised through.

Workup

  1. extractionwas extracted with ether (4×150 mL)
  2. concentrationAfter the solution was concentrated to low volume
  3. dry with materialdried with magnesium sulphate overnight
  4. filtrationfiltered
  5. customthe solvent removed in a vacuum

Sources & evidence

ORD record
ord-1d6c203f17674e049121671e6aedd792
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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