Methyl 2-Phenylisonicotinate → HCID 22831677, compound

HRID 1963228Notes

Reaction equation

HRID 1963228 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][N:16]=2)[C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.[Pt](=O)=O>[C:1]1([CH:7]2[CH2:8][CH:9]([C:10]([O:12][CH3:13])=[O:11])[CH2:14][CH2:15][NH:16]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 12183945Methyl 2-Phenylisonicotinate

Product 1

HCID 22831677HCID 22831677, compoundYield 113.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl 2-phenylisonicotinate (1.83 g, 8.58 mmol) was dissolved in acetic acid (20 mL) and platinum(IV) oxide (0.097 g, 0.43 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 2.5 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 water phase was extracted with DCM and the combined organic phase washed with brine, passed through a phase separator and evaporated to yield crude methyl 2-phenylpiperidine-4-carboxylate (2.131 g) as a yellow oil. MS m/z 220 (M+H)+

Workup

  1. customwas hydrogenated in a Büchi hydrogenator at room temperature
  2. filtrationThe catalyst was filtered off
  3. washwashed with MeOH
  4. additionDCM and 10% K2CO3 were added
  5. customthe phases separated
  6. extractionThe water phase was extracted with DCM
  7. washthe combined organic phase washed with brine
  8. customevaporated

Sources & evidence

ORD record
ord-465f0d406edb4a78826016e6ac3a8053
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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