Hydrochloric Acid → 4-Benzyl-1-(dimethylamino)-4-((dimethylamino)methyl)cyclohexane carbonitrile

HRID 76923Notes

Reaction equation

HRID 76923 reaction equation
[CH3:1][NH:2][CH3:3].[CH2:4]([C:11]1([CH2:18][N:19]([CH3:21])[CH3:20])[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C-:22]#[N:23].[K+].Cl>O.CO>[CH2:4]([C:11]1([CH2:18][N:19]([CH3:21])[CH3:20])[CH2:16][CH2:15][C:14]([N:2]([CH3:3])[CH3:1])([C:22]#[N:23])[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 9032Potassium CyanideHCID 686332214-Benzyl-4-((dimethylamino)methyl)cyclohexanone

Product 1

HCID 686314524-Benzyl-1-(dimethylamino)-4-((dimethylamino)methyl)cyclohexane carbonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

40% aqueous dimethylamine solution (2.8 mL, 22.1 mmol), 4-benzyl-4-((dimethylamino)methyl)cyclohexanone (1.13 g, 4.60 mmol) and potassium cyanide (0.70 g, 11.0 mmol) were added to a mixture of 4N hydrochloric acid (3 mL) and methanol (1.05 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, the residue was taken up in dichloromethane (200 mL) and dried overnight with magnesium sulphate, filtered and the solvent was 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
  3. dry with materialdried overnight with magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed in a vacuum

Sources & evidence

ORD record
ord-a1f67065fc93401c84c485ebc986db04
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

Loading…