Hydrochloric Acid → 2,5-Dichlorobenzoylpiperidine

HRID 1721693Notes

Reaction equation

HRID 1721693 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

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-dichlorobenzoylchoride 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.

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-ee73009bd2b74f94946ed15dd5a3cab9
Source dataset
uspto-grants-1996_04
Patent number
US05512630

Reaction notes

Loading…