HCID 66731996, compound → 2-(4-Trifluoromethyl-phenyl)-piperidine-4-carboxylic acid methyl ester

HRID 1963146Notes

Reaction equation

HRID 1963146 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][N:18]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1>C(O)(=O)C.[Pt](=O)=O>[F:19][C:2]([F:1])([F:20])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:10][CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:16][CH2:17][NH:18]2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 66731996HCID 66731996, compound

Product 1

HCID 667318002-(4-Trifluoromethyl-phenyl)-piperidine-4-carboxylic acid methyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 176Acetic AcidSolvent

Procedure

Methyl 2-(4-(trifluoromethyl)phenyl)isonicotinate (4.985 g, 17.73 mmol) was dissolved in acetic acid (45 mL) and platinum(IV) oxide (0.232 g, 1.02 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 5 h. More platinum(IV) oxide (0.116 g, 0.51 mmol) was added and the hydrogenation continued at 5 bar for 1 h. The catalyst was filtered off and washed with MeOH and the eluate evaporated. DCM and 10% K2CO3 were added and the phases separated. The organic layer was washed with brine, passed through a phase separator and evaporated to yield methyl 2-(4-(trifluoromethyl)phenyl)piperidine-4-carboxylate (5.04 g, 99%) as a brown oil. MS m/z 288 (M+H)+

Workup

  1. customwas hydrogenated in a Büchi hydrogenator at room temperature
  2. waitthe hydrogenation continued at 5 bar for 1 h
  3. filtrationThe catalyst was filtered off
  4. washwashed with MeOH
  5. additionDCM and 10% K2CO3 were added
  6. customthe phases separated
  7. washThe organic layer was washed with brine
  8. customevaporated

Sources & evidence

ORD record
ord-8548f4870321497e955a497b93b8ac65
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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