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

HRID 76913Notes

Reaction equation

HRID 76913 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[CH3:5][N:6]([CH3:20])[C:7]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]1.[C-:21]#[N:22].[K+]>O.CO>[CH3:2][N:3]([CH3:4])[C:10]1([C:21]#[N:22])[CH2:11][CH2:12][C:7]([N:6]([CH3:20])[CH3:5])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH2:9]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

A mixture of methanol (50 ml) and water (50 ml) was acidified with hydrochloric acid (37%, 0.2 ml) and mixed with an aqueous solution of dimethylamine (40%, 11.5 ml, 91 mmol) with ice cooling and stirring. Then 4-dimethylamino-4-phenylcyclohexanone (2.17 g, 10 mmol) and KCN (1.6 g, 24.6 mmol) were added to the solution. A clear solution was formed after 15 min. The ice cooling was removed and the batch stirred for 2.5 h at RT, and a white solid began to separate out after approx. 1 h. The batch was brought to approx. 0° C. again for 1 h by means of ice cooling to complete the precipitation. The precipitate was then separated by means of a fritted glass filter and dried in a vacuum at a bath temperature of 40° C. A diastereoisomer mixture of the title compound was obtained with a yield of 1.83 g (67%) and a melting point of 82-92° C.

Workup

  1. customA clear solution was formed after 15 min
  2. customThe ice cooling was removed
  3. stirringthe batch stirred for 2.5 h at RT
  4. customto separate out after approx. 1 h
  5. customthe precipitation
  6. customThe precipitate was then separated by means of a fritted glass
  7. filtrationfilter
  8. customdried in a vacuum at a bath temperature of 40° C
  9. additionA diastereoisomer mixture of the title compound
  10. customwas obtained with a yield of 1.83 g (67%)

Sources & evidence

ORD record
ord-caf93248468b4c92b6f6ea341d193e11
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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