Hydrochloric Acid → 1-Acetyl-4-(2',4'-difluorobenzoyl)piperidine

HRID 1381860Notes

Reaction equation

HRID 1381860 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:13]([N:16]1[CH2:21][CH2:20][CH:19]([C:22](Cl)=[O:23])[CH2:18][CH2:17]1)(=[O:15])[CH3:14].Cl>ClCCl>[C:13]([N:16]1[CH2:17][CH2:18][CH:19]([C:22](=[O:23])[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[F:8])[CH2:20][CH2:21]1)(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 97411,3-DifluorobenzeneHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27407071-Acetyl-4-(2',4'-difluorobenzoyl)piperidineYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 65 parts of 1,3-difluorobenzene, 130 parts of aluminium chloride and 195 parts of dichloromethane was added dropwise a solution of 95 parts of 1-acetyl-4-piperidine-carbonyl chloride in 65 parts of dichloromethane while cooling. Upon completion, stirring was continued for 3 hours at room temperature. The reaction mixture was poured into a mixture of crushed ice and hydrochloric acid. The product was extracted with dichloromethane. The organic layer was dried, filtered and evaporated, yielding 48 parts (36%) of 1-acetyl-4-(2,4-difluorobenzoyl)piperidine as a residue (intermediate 1).

Workup

  1. temperaturewhile cooling
  2. extractionThe product was extracted with dichloromethane
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-c538b26e05fd4af48170b063c01f5ac8
Source dataset
uspto-grants-1989_02
Patent number
US04804663

Reaction notes

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