Hydrochloric Acid → 2,5-Dichlorobenzoylpiperidine

HRID 399885

Reaction equation

HRID 399885 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.Cl>[Cl-].[Al+3].[Cl-].[Cl-].C1(C)C=CC=CC=1.N1C=CC=CC=1.C1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:5].[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:5]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 8083MorpholineHCID 179452,5-Dichlorobenzoyl chloride

Product 2

HCID 8682952,5-DichlorobenzoylpiperidineHCID 868908(2,5-Dichlorophenyl)(morpholino)methanone

Reagents, catalysts & solvents 4

HCID 6451240Aluminum(III) ChlorideCatalystHCID 241BenzeneSolventHCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

2,5-dichlorobenzoyl-containing compounds (e.g. 2,5-dichlorobenzophenones and 2,5-dichlorobenzamides) can be readily prepared from 2,5-dichlorobenzoylchloride. Pure 2,5-dichlorobenzoylchloride is obtained by vacuum distillation of the mixture obtained from the reaction of commercially available 2,5-dichlorobenzoic acid with a slight excess of thionyl chloride in refluxina toluene. 2,5-dichlorobenzophenones (2,5-dichlorobenzcphenone, 2,5-dichloro-4'-methylbenzophenone,2,5-dichloro-4'-meth-oxybenzophenone, and 2,5-dichloro-4'-phenoxy-benzo-phenone) are prepared by the Friedel-Crafts benzoylations of benzene and substituted benzenes (e.g. toluene, anisole, diphenyl ether), respectively, with 2,5-dichlorobenzoylchloride at 0°-5° C. using 2-3 mol equivalents of aluminum chloride as a catalyst. The solid products obtained upon quenching with water are purified by recrystallization from toluene/hexanes. 2,5-dichlorobenzoylmorpholine and 2,5-dichlorobenzoylpiperidine are prepared from the reaction of 2,5-dichlorobenzoylchloride and either morpholine or piperidine, respectively, in toluene with pyridine added to trap the HCl that is evolved. After washing away the pyridinium salt and any excess amine, the product is crystallized from the toluene solution.

Workup

  1. customat 0°-5° C.
  2. customThe solid products obtained
  3. customupon quenching with water
  4. customare purified by recrystallization from toluene/hexanes
  5. washAfter washing away the pyridinium salt
  6. customany excess amine, the product is crystallized from the toluene solution

Sources & evidence

ORD record
ord-a5924c01ba5145b38c69b331d72d6630
Source dataset
uspto-grants-1998_10
Patent number
US05824744

Linked notes

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