Hydrochloric Acid → 4-Dimethylamino-4-(4-methoxy-phenyl)-1-methylamino-cyclohexane carbonitrile

HRID 76944Notes

Reaction equation

HRID 76944 reaction equation
[CH3:1][NH2:2].Cl.[CH3:4][N:5]([CH3:21])[C:6]1([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]1.[C-:22]#[N:23].[K+]>CO.O>[CH3:4][N:5]([CH3:21])[C:6]1([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH2:11][CH2:10][C:9]([NH:23][CH3:22])([C:1]#[N:2])[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 9032Potassium CyanideHCID 125956454-(Dimethylamino)-4-(4-methoxyphenyl)cyclohexan-1-one

Product 1

HCID 686308414-Dimethylamino-4-(4-methoxy-phenyl)-1-methylamino-cyclohexane carbonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

40% aqueous methylamine solution (3.50 mL, 40.1 mmol) was added in drops to a mixture of 4N hydrochloric acid (1.98 mL) and methanol (2.3 mL) with ice cooling. A solution of the title compound from step 2 (2.00 mg, 8.09 mmol) in methanol (30 mL) and potassium cyanide (1.32 g, 20.3 mmol) were then added. The mixture was stirred for 3 d at RT and then after adding water (10 mL) was extracted 4× with ether. The combined organic phases were dried over Na2SO4 and concentrated to low volume in a vacuum.

Workup

  1. extractionwas extracted 4× with ether
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated to low volume in a vacuum

Sources & evidence

ORD record
ord-86c91fdc26534bccb1a0d100f4272cf4
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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