Benzonitrile → HCID 13431722, compound

HRID 1762224Notes

Reaction equation

HRID 1762224 reaction equation
[NH:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si](Cl)(Cl)(Cl)Cl.[C:20](#[N:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+]>ClCCCl.O.CO>[CH3:14][N:11]1[CH2:12][CH2:13][CH:8]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=2[C:20](=[NH:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:9][CH2:10]1

Participants

8

Reactant 4

HCID 7505BenzonitrileHCID 14798Sodium HydroxideHCID 24816Silicon tetrachlorideHCID 896421-Methyl-N-phenylpiperidin-4-amine

Product 1

HCID 13431722HCID 13431722, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.38 g (2 mmol) of 4-anilino-1-methyl-piperidine 1 dissolved in 10 ml of 1.2-dichloroethane are added 0.3 ml (2×1.2 mmol) of boron trifluoride ether adduct, 0.28 ml (2×1.2 mmol) of silicon tetrachloride, and 0.41 ml (2×2 mmol) of benzonitrile at room temperature with stirring, and the mixture is heated under reflux with stirring for 20 hours. The reaction mixture is cooled and a solution of 2.5 g of sodium hydroxide dissolved in 10 ml of water and 4 ml of methanol are added thereto with stirring under ice-cooling. The mixture is stirred at room temperature for 1 hour and extracted with dichloromethane; the organic layer is washed with water, dried over anhydrous magnesium sulfate, and concentrated. The resulting residue is recrystallized from ether-petroleum ether to give 414 mg of crystalline 2-(1-methyl-4-piperidinyl)aminobenzophenone imine 2.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux
  3. stirringwith stirring for 20 hours
  4. temperatureThe reaction mixture is cooled
  5. stirringwith stirring under ice-
  6. temperaturecooling
  7. stirringThe mixture is stirred at room temperature for 1 hour
  8. extractionextracted with dichloromethane
  9. washthe organic layer is washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated
  12. customThe resulting residue is recrystallized from ether-petroleum ether

Sources & evidence

ORD record
ord-faddd23ce8cd4d2aa7b4846a55b568b8
Source dataset
uspto-grants-1989_05
Patent number
US04831132

Reaction notes

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