Methyl 2-(3-(trifluoromethyl)benzyl)isonicotinate → Methyl 2-(3-(trifluoromethyl)benzyl)piperidine-4-carboxylate

HRID 1963284Notes

Reaction equation

HRID 1963284 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][N:16]=1)[C:10]([O:12][CH3:13])=[O:11]>[Pt](=O)=O.C(O)(=O)C>[F:20][C:2]([F:1])([F:21])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][CH:7]1[CH2:8][CH:9]([C:10]([O:12][CH3:13])=[O:11])[CH2:14][CH2:15][NH:16]1

Participants

4

Reactant 1

HCID 66732099Methyl 2-(3-(trifluoromethyl)benzyl)isonicotinate

Product 1

HCID 66731790Methyl 2-(3-(trifluoromethyl)benzyl)piperidine-4-carboxylateYield 110%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl 2-(3-(trifluoromethyl)benzyl)isonicotinate (12.83 g, 43.45 mmol) and platinum(IV) oxide (0.197 g, 0.87 mmol) were added to acetic acid (150 mL). The reaction mixture was hydrogenated in a Büchi hydrogenator for 6 h at room temperature and 5 bar. The catalyst was filtered off and fresh platinum(IV) oxide (0.26 g) was added. Hydrogenation was continued overnight at 6 bar. The catalyst was filtered off and the solvent was evaporated. The residue was dissolved in ethyl acetate and washed with Na2CO3 (aq). The organic layer was isolated, dried over MgSO4, filtered through celite and the solvent evaporated. Crude methyl 2-(3-(trifluoromethyl)benzyl)piperidine-4-carboxylate (14.4 g, 110%) was isolated.

Workup

  1. filtrationThe catalyst was filtered off
  2. additionfresh platinum(IV) oxide (0.26 g) was added
  3. waitHydrogenation was continued overnight at 6 bar
  4. filtrationThe catalyst was filtered off
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with Na2CO3 (aq)
  8. customThe organic layer was isolated
  9. dry with materialdried over MgSO4
  10. filtrationfiltered through celite
  11. customthe solvent evaporated

Sources & evidence

ORD record
ord-8541f13d7edd4269a6c44d34ddda269a
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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