Trifluoromethanesulfonate → HCID 411460, compound

HRID 1656388Notes

Reaction equation

HRID 1656388 reaction equation
FC(F)(F)S([O-])(=O)=O.[CH3:9][N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]1[C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[Pt]=O.C(O)(=O)C>[OH:23][CH:16]([CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][N:10]1[CH3:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 2758875TrifluoromethanesulfonateHCID 19788053HCID 19788053, compound

Product 1

HCID 411460HCID 411460, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

The trifluoromethanesulfonate salt of N-methyl-2-benzoylpyridine (23.2 g, 0.066 mol) was added to a Parr bottle containing platinum oxide (0.20 g) and acetic acid (100 ml). Hydrogenation was stopped after 8 hours and a 299 psi drop in pressure. The reaction mixture was filtered. The filtrate was concentrated using a rotovap and poured onto ice. It was basified using 25% sodium hydroxide to pH 11. This aqueous mixture was extracted with ethyl acetate. The organic layer was washed with a small amount of water and brine. It was dried over potassium carbonate, filtered and stripped. The residue was dissolved in toluene and filtered. The toluene was stripped using the rotovap leaving 12.1 g (88% yield) 2-(α-hydroxybenzyl)-N-methylpiperidine.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated
  3. additionpoured onto ice
  4. extractionThis aqueous mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with a small amount of water and brine
  6. dry with materialIt was dried over potassium carbonate
  7. filtrationfiltered
  8. dissolutionThe residue was dissolved in toluene
  9. filtrationfiltered

Sources & evidence

ORD record
ord-5e92a33f0b554169b811a53ea7cf6a06
Source dataset
uspto-grants-1993_10
Patent number
US05254569

Reaction notes

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