Hydrochloric Acid → 2,5-Dichlorobenzoylpiperidine

HRID 2929

Reaktionsgleichung

Reaktionsgleichung von HRID 2929
C1(OC)C=CC=CC=1.C1(OC2C=CC=CC=2)C=CC=CC=1.[Cl:22][C:23]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:24]=1[C:25](Cl)=[O:26].[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.[NH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1.Cl>[Cl-].[Al+3].[Cl-].[Cl-].C1(C)C=CC=CC=1.N1C=CC=CC=1.C1C=CC=CC=1>[Cl:22][C:23]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:24]=1[C:25]([N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)=[O:26].[Cl:22][C:23]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:24]=1[C:25]([N:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1)=[O:26]

Komponenten

12

Edukt 6

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 7583Diphenyl EtherHCID 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 1140TolueneLösungsmittel3×

Versuchsvorschrift

A wide variety of 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 refluxing toluene. 2,5-dichlorobenzophenones (e.g. 2,5-dichlorobenzophenone, 2,5-dichloro-4'-methylbenzophenone, 2,5-dichloro-4'-methoxybenzophenone, and 2,5-dichloro-4'-phenoxybenzophenone) are prepared by the Friedel-Crafts benzoylations of an excess of benzene or substituted benzenes (e.g. toluene, anisole, or diphenyl ether, respectively) with 2,5-dichlorobenzoylchloride at 0-5° C. using 2-3 mole 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-dichloro-benzoylpiperidine are prepared from the reaction of 2,5-dichloro-benzoylchloride and either morpholine or piperidine, respectively, in toluene with pyridine added to trap the hydrogen chloride 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-f6bb4c0c2bb1418fb1a1edbd930b2162
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731400

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