(Pyridin-4-yl)[3-(trifluoromethyl)phenyl]methanone → ALPHA-[3-(TRIFLUOROMETHYL)PHENYL]-4-PIPERIDINEMETHANOL

HRID 2397469Notes

Reaction equation

HRID 2397469 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[C:6]([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)=[O:7].[H][H]>CO.Cl.[Pt]=O>[OH:7][CH:6]([CH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1)[C:5]1[CH:14]=[CH:15][CH:16]=[C:3]([C:2]([F:1])([F:17])[F:18])[CH:4]=1

Participants

6

Reactant 2

HCID 21438388(Pyridin-4-yl)[3-(trifluoromethyl)phenyl]methanoneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11392289ALPHA-[3-(TRIFLUOROMETHYL)PHENYL]-4-PIPERIDINEMETHANOL

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 25.1 g (0.1 mole) of 4-(m-trifluoromethylbenzoyl)pyridine in 150 ml methanol and 10 ml concentrated hydrochloric acid was shaken with one gram of platinum oxide at an initial pressure of fifty psi of hydrogen. The hydrogen uptake was complete in ten hours. The catalyst was filtered off. After removal of the methanol under reduced pressure, the residue was dissolved in water and made basic with sodium hydroxide. Extraction with benzene and concentration of the benzene solution gave crude 4-(alpha-hydroxy-m-trifluoromethylbenzyl)piperidine. Yield 20.2 grams.

Workup

  1. filtrationThe catalyst was filtered off
  2. customAfter removal of the methanol under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. extractionExtraction with benzene and concentration of the benzene solution

Sources & evidence

ORD record
ord-3d4de6eb1dd9463faaabceb87b8da30f
Source dataset
uspto-grants-1977_05
Patent number
US04021564

Reaction notes

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