Hydrochloric Acid → 4-Dimethylamino-1-methylamino-4-phenyl-cyclohexane carbonitrile

HRID 76915Notes

Reaction equation

HRID 76915 reaction equation
[CH3:1][NH2:2].[CH3:3][N:4]([CH3:18])[C:5]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1.Cl.[C-:20]#[N:21].[K+]>CO.O>[CH3:3][N:4]([CH3:18])[C:5]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH2:9][C:8]([NH:21][CH3:20])([C:1]#[N:2])[CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 9032Potassium CyanideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 686329644-Dimethylamino-1-methylamino-4-phenyl-cyclohexane carbonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

40% aqueous methylamine solution (8.7 mL, 69 mmol) and 4-dimethylamino-4-phenylcyclohexanone (3.13 g, 14.4 mmol) dissolved in methanol (15 mL) were added to a solution of 4N hydrochloric acid (3.75 mL) and methanol (2.25 mL) cooled to 0° C. The reaction mixture was then mixed with potassium cyanide (2.25 g, 34 mmol) and stirred for 5 d at RT. For work up the mixture was mixed with water (60 mL) and extracted with ether (3×50 ml). The combined organic phases were dried with sodium sulphate and concentrated to low volume in a vacuum.

Workup

  1. extractionextracted with ether (3×50 ml)
  2. dry with materialThe combined organic phases were dried with sodium sulphate
  3. concentrationconcentrated to low volume in a vacuum

Sources & evidence

ORD record
ord-ee91c056fb8c48b4b1602bea14c26809
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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