Piperidine → 1-(4-Fluorophenyl)-4-methyl-2-phenyl-penten-3-one

HRID 1609563Notes

Reaction equation

HRID 1609563 reaction equation
N1CCCCC1.[F:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1.[CH:16]([C:19]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20])([CH3:18])[CH3:17]>C1(C)C=CC=CC=1>[F:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19](=[O:20])[CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 680234-FluorobenzaldehydeHCID 76163Benzyl isopropyl ketone

Product 1

HCID 544349341-(4-Fluorophenyl)-4-methyl-2-phenyl-penten-3-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.9 ml of piperidine is added to 24.8 g (0.2 mol) of 4-fluorobenzaldehyde and 32.4 g (0.2 mol) of benzyl isopropyl ketone in 150 ml of toluene and the mixture is heated to reflux overnight. After cooling to room temperature, the mixture is extracted several times using water and the organic phase is dried over magnesium sulphate and concentrated in vacuo. The residue is subjected to incipient distillation up to a bath temperature of 150° C. at 0.1 mbar in a high vacuum and 43.8 g of crude product are obtained in the distillation residue.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux overnight
  3. extractionthe mixture is extracted several times
  4. dry with materialthe organic phase is dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. distillationdistillation up to a bath temperature of 150° C. at 0.1 mbar in a high vacuum and 43.8 g of crude product
  7. customare obtained in the distillation residue

Sources & evidence

ORD record
ord-2cc95da6d8a14918818e429d848217a4
Source dataset
uspto-grants-1995_03
Patent number
US05401746

Reaction notes

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