Pyridine → Moperone

HRID 1578390Notes

Reaction equation

HRID 1578390 reaction equation
N1C=CC=CC=1.[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:32])[CH2:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][C:21]([OH:31])([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[CH:10][CH:9]=1>[O-2].[O-2].[O-2].[Cr+6].O>[OH:31][C:21]1([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][CH2:15][C:14]([C:11]2[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=2)=[O:32])[CH2:19][CH2:20]1

Participants

5

Reactant 2

HCID 1049PyridineHCID 21560004HCID 21560004, compound

Product 1

HCID 4249Moperone

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

One gram of chromium trioxide was added with stirring to 40 ml of pyridine cooled to 0°C. The mixture was stirred at room temperature for 1 hour, and then again cooled to 0°C. Into the said mixture was added 1.1 g of 1-(p-fluorophenyl)-4-[4-hydroxy-4-(p-methylphenyl)-piperidino]-1-butanol, and the mixture was stirred for 1 hour under cooling with ice. The reaction mixture was poured into 300 ml of cold water to separate an oily substance. The oily substance is extracted with ethyl acetate, and the ethyl acetate layer was washed 4 times with each 60 ml of water, dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The residue was recrystallized from aqueous acetone to obtain γ-(4-hydroxy-4-p-methylphenylpiperidino)-p-fluorobutyrophenone, melting at 119° - 120°C.

Workup

  1. temperatureagain cooled to 0°C
  2. stirringthe mixture was stirred for 1 hour
  3. temperatureunder cooling with ice
  4. customto separate an oily substance
  5. extractionThe oily substance is extracted with ethyl acetate
  6. washthe ethyl acetate layer was washed 4 times with each 60 ml of water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe residue was recrystallized from aqueous acetone

Sources & evidence

ORD record
ord-609c5a335900419bb42c2459dfbc788e
Source dataset
uspto-grants-1976_02
Patent number
US03936468

Reaction notes

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