Hydrochloric Acid → 4-Dimethylamino-4-phenyl-1-(pyrrolidin-1-yl)cyclohexane carbonitrile

HRID 76914Notes

Reaction equation

HRID 76914 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:7][N:8]([CH3:22])[C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1.[C-:23]#[N:24].[K+]>O.CO>[CH3:7][N:8]([CH3:22])[C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH2:13][C:12]([N:2]2[CH2:6][CH2:5][CH2:4][CH2:3]2)([C:23]#[N:24])[CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 31268PyrrolidineHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 686307854-Dimethylamino-4-phenyl-1-(pyrrolidin-1-yl)cyclohexane 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 pyrrolidine (7.5 ml, 91 mmol) with ice cooling and stirring. 4-dimethylamino-4-phenylcyclohexanone (2.17 g, 10 mmol) was then added to the solution. The batch was stirred for 10 min to dissolve the ketone as completely as possible. KCN (1.6 g, 24.6 mmol) was then added. The ice cooling was removed and the batch stirred for 2 d at RT, during which white solid separated out. The batch was brought to approx. 0° C. again for 1 h by 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 2.7 g (90%) and with a melting point of 136-142° C.

Workup

  1. stirringThe batch was stirred for 10 min
  2. customThe ice cooling was removed
  3. stirringthe batch stirred for 2 d at RT, during which white solid
  4. customseparated out
  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 2.7 g (90%) and with a melting point of 136-142° C.

Sources & evidence

ORD record
ord-673e9c9753ab4c54856111ddebd2f13b
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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