4-Chlorobenzoyl chloride → 1-(4-Chlorobenzoyl)piperidin-4-one

HRID 129078

Reaction equation

HRID 129078 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O.Cl.[NH:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1>O.O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:19]2[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 11430Potassium CarbonateHCID 2723901Piperonylamine

Product 1

HCID 152314041-(4-Chlorobenzoyl)piperidin-4-oneYield 74.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

87.5 g of 4-chlorobenzoyl chloride and a solution of 276 g of potassium carbonate in 552 ml of water cooled to 5° C. are added successively with stirring to a suspension of 80.6 g of powdered 4-piperidone hydrochloride hydrate in 1 l of tetrahydrofuran. The mixture is stirred at ambient temperature for a further 45 minutes. The organic phase is then separated off, the aqueous phase is extracted twice more with ethyl acetate, and the organic phases are combined, dried and evaporated down. The residue is dissolved in ethyl acetate and the solution is treated with petroleum ether. 88.6 g of the title compound of melting point 61°-63° C. are obtained.

Workup

  1. additionare added successively
  2. customThe organic phase is then separated off
  3. extractionthe aqueous phase is extracted twice more with ethyl acetate
  4. customdried
  5. customevaporated down
  6. dissolutionThe residue is dissolved in ethyl acetate
  7. additionthe solution is treated with petroleum ether

Sources & evidence

ORD record
ord-6d7f17500ad642cb9fadff2d9312fea8
Source dataset
uspto-grants-1995_11
Patent number
US05466687

Linked notes

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