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Hydrochloric Acid → 2,5-Dichlorobenzoylpiperidine

HRID 400258
ノート
印刷プレビュー

反応式

HRID 400258 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

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

生成物 2

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

試薬・触媒・溶媒 4

HCID 6451240
Aluminum(III) Chloride
触媒
HCID 241Benzene溶媒
HCID 1049Pyridine溶媒
HCID 1140Toluene溶媒2 回

実験手順

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 (2,5-dichlorobenzophenone, 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-dichloro-benzoylpiperidine 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.

後処理

  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

出典と根拠

ORDレコード
ord-33ff48109f5c40dfa17c6374646dd058
出典データセット
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05827927

反応ノート

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