Hydrochloric Acid → 2,5-Dichlorobenzoylpiperidine

HRID 264586

Reaction equation

HRID 264586 reaction equation
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]

Participants

12

Reactant 6

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 7583Diphenyl EtherHCID 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 1140TolueneSolvent3×

Procedure

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.

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-dace64c53ffc4a46b329f39b0c2989ff
Source dataset
uspto-grants-1997_07
Patent number
US05646232

Linked notes

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