Hydrochloric Acid → 1-Acetyl-4-(4-fluorobenzoylmethyl)piperidine

HRID 126859Notes

Reaction equation

HRID 126859 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Cl-].[Cl-].[Al+3].[C:12]([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22](Cl)=[O:23])[CH2:17][CH2:16]1)(=[O:14])[CH3:13].Cl>>[C:12]([N:15]1[CH2:16][CH2:17][CH:18]([CH2:21][C:22]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:23])[CH2:19][CH2:20]1)(=[O:14])[CH3:13]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 10008Fluorobenzene2×HCID 6451240Aluminum(III) ChlorideHCID 202880651-Acetyl-4-piperidineacetyl chloride

Product 1

HCID 100841181-Acetyl-4-(4-fluorobenzoylmethyl)piperidineYield 90%

Procedure

To a stirred mixture of 50 parts of fluorobenzene and 32 parts of aluminium trichloride is added dropwise (slowly) a solution of 26.5 parts of 1-acetyl-4-piperidineacetyl chloride in 50 parts of fluorobenzene. Upon completion, stirring is continued for 2 hours at reflux temperature. The reaction mixture is cooled to room temperature and poured onto a mixture of crushed ice and a hydrochloric acid solution. The aqueous phase is separated and extracted with methylbenzene. The combined organic phases are dried, filtered and evaporated, yielding 31 parts (90%) of 2-(1-acetyl-4-piperidinyl)-1-(4-fluorophenyl)ethanone as a residue.

Workup

  1. temperatureat reflux temperature
  2. additionpoured onto a mixture of crushed ice
  3. customThe aqueous phase is separated
  4. extractionextracted with methylbenzene
  5. customThe combined organic phases are dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-deff6adbd6dd4941877d77179a7d9674
Source dataset
uspto-grants-1981_03
Patent number
US04254127

Reaction notes

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