Methyl 2-(2-fluorobenzyl)isonicotinate → Methyl 2-(2-fluorobenzyl)piperidine-4-carboxylate

HRID 1963275Notes

Reaction equation

HRID 1963275 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][N:14]=1)[C:8]([O:10][CH3:11])=[O:9]>C(O)(=O)C.[Pt](=O)=O>[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][CH:5]1[CH2:6][CH:7]([C:8]([O:10][CH3:11])=[O:9])[CH2:12][CH2:13][NH:14]1

Participants

4

Reactant 1

HCID 66732036Methyl 2-(2-fluorobenzyl)isonicotinate

Product 1

HCID 66732347Methyl 2-(2-fluorobenzyl)piperidine-4-carboxylateYield 81%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl 2-(2-fluorobenzyl)isonicotinate (5.42 g, 22.08 mmol) was dissolved in acetic acid (50 mL) and platinum(IV) oxide (0.251 g, 1.10 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator for 4 h at room temperature and 5 bar. 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 water, passed through a phase separator and evaporated to yield methyl 2-(2-fluorobenzyl)piperidine-4-carboxylate (4.49 g, 81%) MS m/z 252 (M+H)+

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with MeOH
  3. additionDCM and 10% K2CO3 were added
  4. customthe phases separated
  5. extractionThe water phase was extracted with DCM
  6. washthe combined organic phase washed with water
  7. customevaporated

Sources & evidence

ORD record
ord-a749f65133a048a6b536acecc4b8d04d
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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