Potassium Hydroxide → 4-(1-Benzylpiperidin-4-ylidenemethyl)benzamide

HRID 2308082Notes

Reaction equation

HRID 2308082 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1)#[N:2].P(OCC)(OCC)[O:12]CC.[CH2:21]([N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][C:29]1=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH-].[K+]>O.C(O)C.C1(C)C=CC=CC=1>[CH2:21]([N:28]1[CH2:33][CH2:32][C:31](=[CH:7][C:6]2[CH:9]=[CH:10][C:3]([C:1]([NH2:2])=[O:12])=[CH:4][CH:5]=2)[CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 31215Triethyl phosphiteHCID 869964-(Bromomethyl)benzonitrileHCID 51700761-Benzyl-2-piperidone

Product 1

HCID 99225744-(1-Benzylpiperidin-4-ylidenemethyl)benzamideYield 43.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

4-Cyanobenzyl bromide (4.90 g, 25.0 mmol), triethyl phosphite (4.77 mL, 27.5 mmol) and toluene (4.9 mL) were charged, and the mixture was stirred with heating under reflux for 3 hrs., while distilling away the solvent at normal pressure. The mixture was allowed to return to room temperature, and concentrated under reduced pressure to give a colorless transparent oil which solidified by standing. N-benzylpiperidone (4.73 g, 25.0 mmol), ethanol (35 mL), water (451 mg, 25.0 mmol) and potassium hydroxide (pellet, 7.01 g, 125 mmol) were added successively, and the mixture was stirred at room temperature for 30 min. to give a yellow solution. The solution was stirred at 65-70° C. for 2 hrs. and cooled to 60° C. to allow precipitation of crystals to give a yellow suspension. Iced water (200 mL) was added, and the mixture was stirred at 0-5° C. After dissolution once, a yellow suspension was formed. The suspension was stirred at 0-5° C. for 30 min. and the crystals were collected by filtration and dried in vacuo at 40° C. to give the title compound (3.30 g, yield 43.0%) as white crystals.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hrs
  3. distillation, while distilling away the solvent at normal pressure
  4. customto return to room temperature
  5. concentrationconcentrated under reduced pressure
  6. customto give a colorless transparent oil which
  7. stirringthe mixture was stirred at room temperature for 30 min.
  8. customto give a yellow solution
  9. stirringThe solution was stirred at 65-70° C. for 2 hrs
  10. customprecipitation of crystals
  11. customto give a yellow suspension
  12. stirringthe mixture was stirred at 0-5° C
  13. dissolutionAfter dissolution once
  14. customa yellow suspension was formed
  15. stirringThe suspension was stirred at 0-5° C. for 30 min.
  16. filtrationthe crystals were collected by filtration
  17. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-3e987743f22345c9a4863af1086606e5
Source dataset
uspto-grants-2004_12
Patent number
US06833457B1

Reaction notes

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