Hydrochloric Acid → 2,5-Dichlorobenzoylpiperidine

HRID 362551

반응식

HRID 362551 반응식
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]

참가 물질

12

반응물 6

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 7583Diphenyl EtherHCID 8082PiperidineHCID 8083MorpholineHCID 179452,5-Dichlorobenzoyl chloride

생성물 2

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

시약·촉매·용매 4

HCID 6451240Aluminum(III) Chloride촉매HCID 241Benzene용매HCID 1049Pyridine용매HCID 1140Toluene용매3회

실험 절차

2,5-dichlorobenzoyl-containing compounds (e.g. 2,5-dichlorobenzoylchloride and 2,5-dichlorobenzoylchloride) 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'-methoxybenzophenone, and 2,5-dichloro-4'-phenoxybenzophenone) 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 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-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.

후처리

  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

출처 및 근거

ORD 기록
ord-507eeb5358734935aaabd7548ef22ff7
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05869592

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