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

HRID 1699649Notes

Reaction equation

HRID 1699649 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 of mixture of 56 ml of 1,3-difluorobenzene, 130 g of aluminium chloride and 147 ml of dichloromethane, a solution of 95 g of 1-acetyl-4-piperidinecarbonyl chloride in 50 ml of dichloromethane was added dropwise while cooling. Upon completion, stirring was continued for 3 hours at room temperature. The reaction mixture was poured out 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 g (36%) of 1-acetyl-4-(2,4-difluorobenzoyl)piperidine as a residue (interm. 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-316be4f38d2f4295a4966913ccbd2ea2
Source dataset
uspto-grants-2002_02
Patent number
US06348457B1

Reaction notes

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