Fluorobenzene → HCID 21939813, compound

HRID 1242912Notes

Reaction equation

HRID 1242912 reaction equation
S(Cl)(Cl)=O.[C:5]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)(=[O:7])[CH3:6].[Cl-].[Al+3].[Cl-].[Cl-].[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:5]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([C:25]2[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=2)=[O:16])[CH2:9]1)(=[O:7])[CH3:6]

Participants

5

Reactant 4

HCID 10008FluorobenzeneHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 140438961-Acetyl-3-piperidinecarboxylic acid

Product 1

HCID 21939813HCID 21939813, compound

Procedure

Thionyl chloride (2.12 ml, 32.1 mmol) was added to fluorobenzene solution (20 ml) of 1-acetyl-3-piperidinecarboxylic acid (5.00 g, 29.2 mmol) under ice-cooling, which was stirred at room temperature for 30 minutes. Aluminum chloride (9.74 g, 73.0 mmol) was added to the solution, which was stirred at 90° C. for 1 hour. The reaction mixture was poured in ice, and extraction was conducted using ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, saturated sodium hydrogencarbonate solution, and again saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting oily substance was purified by silica gel column chromatography (development solvent; hexane:ethyl acetate=1:1), to give (1-acetyl-3-piperidinyl)(4-fluorophenyl)methanone (4.93 g).

Workup

  1. temperaturecooling
  2. stirringwas stirred at 90° C. for 1 hour
  3. additionThe reaction mixture was poured in ice
  4. extractionextraction
  5. washThe extract was washed with saturated aqueous sodium chloride solution, saturated sodium hydrogencarbonate solution, and again saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled out under reduced pressure
  8. customThe resulting oily substance was purified by silica gel column chromatography (development solvent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-93185d6358e24a2fbd191c741a8ee011
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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