Potassium Iodide → 1-[(4-Chlorophenyl)methyl]piperidin-4-one

HRID 1017324Notes

Reaction equation

HRID 1017324 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1>CCC(=O)CC>[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:1]2[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 10796Cesium carbonateHCID 337214-Piperidone

Product 1

HCID 105610671-[(4-Chlorophenyl)methyl]piperidin-4-one

Reagents, catalysts & solvents 1

HCID 7288Ethyl ketoneSolvent

Procedure

Dissolve 4-piperidone (17 mmol) in 3-pentanone (25 mL) and heat to reflux. Add cesium carbonate (19 mmol) and a catalytic amount of potassium iodide, followed by 4-chlorobenzyl chloride (20 mmol). Stir and reflux for 4 hours. Filter the hot suspension, wash the residue with hot acetone (4×20 mL), combine the filtrate and washings, and evaporate the solvent in vacuo to give the title compound.

Workup

  1. temperatureheat to reflux
  2. temperaturereflux for 4 hours
  3. filtrationFilter the hot suspension
  4. washwash the residue with hot acetone (4×20 mL)
  5. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-c3925eaacd6944619a8750dcf5c5fb73
Source dataset
uspto-grants-2002_11
Patent number
US06479487B1

Reaction notes

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