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Hydrochloric Acid → 2,5-Dichlorobenzoylpiperidine

HRID 399885
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 399885
[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]
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Komponenten

10

Edukt 4

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

Produkt 2

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

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6451240Aluminum(III) ChlorideKatalysatorHCID 241BenzeneLösungsmittelHCID 1049PyridineLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a5924c01ba5145b38c69b331d72d6630
Quelldatensatz
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05824744

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