HCID 66731903, compound → HCID 66732196, compound

HRID 1963209Notes

Reaction equation

HRID 1963209 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][N:21]=2)[C:15]([O:17][CH3:18])=[O:16])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9]>C(O)(=O)C.[Pt](=O)=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:12]2[CH2:13][CH:14]([C:15]([O:17][CH3:18])=[O:16])[CH2:19][CH2:20][NH:21]2)[CH:5]=[CH:6][C:7]=1[C:8]([F:9])([F:10])[F:11]

Participants

4

Reactant 1

HCID 66731903HCID 66731903, compound

Product 1

HCID 66732196HCID 66732196, compoundYield 110%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl 2-(3-methyl-4-(trifluoromethyl)phenyl)isonicotinate (2.32 g, 7.86 mmol) was dissolved in acetic acid (150 mL) and platinum(IV) oxide (36 mg, 0.16 mmol) was added. Hydrogenation in a Büchi hydrogenator at room temperature and 6 bar for 2 h. The catalyst was filtered off. More platinum(IV) oxide was added and hydrogenation continued until starting material was consumed. Catalyst was filtered off and the solvent was evaporated to yield crude methyl 2-(3-methyl-4-(trifluoromethyl)phenyl)piperidine-4-carboxylate (2.60 g, 110%).

Workup

  1. filtrationThe catalyst was filtered off
  2. additionMore platinum(IV) oxide was added
  3. customwas consumed
  4. filtrationCatalyst was filtered off
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-070d4c8c2a8b477989a266daae00ce57
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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