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

HRID 2308080Notes

Reaction equation

HRID 2308080 reaction equation
Cl[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][CH:4]=1.P(OCC)(OCC)OCC.[I-].[K+].[CH2:24]([N:31]1[CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CC(C)([O-])C.[K+]>O.CN(C)C=O.C(#N)C>[CH2:24]([N:31]1[CH2:36][CH2:35][C:34](=[CH:2][C:3]2[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][CH:4]=2)[CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 192201-Benzyl-4-piperidoneHCID 31215Triethyl phosphiteHCID 4583634-(Chloromethyl)benzamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 99225744-(1-Benzylpiperidin-4-ylidenemethyl)benzamideYield 85.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

The compound (25.0 g, 0.147 mol) obtained in Example 1, triethyl phosphite (29.4 g, 0.177 mol), potassium iodide (22.0 g, 0.133 mol) and acetonitrile (125 mL) were charged and stirred under reflux for 3 hrs. The reaction mixture was allowed to return to room temperature, and concentrated under reduced pressure. To the residue were added N,N-dimethylformamide (100 mL) and 1-benzyl-4-piperidone (30.6 g, 0.162 mol), and the mixture was stirred under ice-cooling. Potassium t-butoxide (23.1 g, 0.206 mol) was added in 3 portions at 15 min. intervals. The reaction mixture was stirred at room temperature for 45 min. Water (400 mL) was dropwise added under ice-cooling, and the mixture was stirred for 30 min. Crystals were collected by filtration, washed with cold water (180 mL) and dried in vacuo at 40° C. to give the title compound (38.7 g, yield 85.2%) as pale-yellow powdery crystals.

Workup

  1. temperatureunder reflux for 3 hrs
  2. customto return to room temperature
  3. concentrationconcentrated under reduced pressure
  4. stirringthe mixture was stirred under ice-
  5. temperaturecooling
  6. stirringThe reaction mixture was stirred at room temperature for 45 min
  7. temperaturecooling
  8. stirringthe mixture was stirred for 30 min
  9. filtrationCrystals were collected by filtration
  10. washwashed with cold water (180 mL)
  11. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-3199c89afae1470db73480928b5ce3e1
Source dataset
uspto-grants-2004_12
Patent number
US06833457B1

Reaction notes

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