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

HRID 1963259Notes

Reaction equation

HRID 1963259 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH2:7][C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][N:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1>C(O)(=O)C.[Pt](=O)=O>[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH2:7][CH:8]2[CH2:9][CH:10]([C:11]([O:13][CH3:14])=[O:12])[CH2:15][CH2:16][NH:17]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 66731796Methyl 2-(4-fluorophenethyl)isonicotinate

Product 1

HCID 66731797Methyl 2-(4-fluorophenethyl)piperidine-4-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl 2-(4-fluorophenethyl)isonicotinate (3.8 g, 14.66 mmol) dissolved in acetic acid (150 mL) and platinum(IV) oxide (0.25 g, 1.10 mmol) was added. The mixture was hydrogenated in a Büchi hydrogenation apparatus at 5 bar and room temperature for 5 h. The catalyst was removed by filtration and the solvent was evaporated. The residue was taken up in DCM and washed with satd NaHCO3. The organic phase was filtered through a phase separator and evaporated. Methyl 2-(4-fluorophenethyl)piperidine-4-carboxylate (3.89 g, quant.) was isolated. MS m/z 266 (M+H)+

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated
  3. washwashed with satd NaHCO3
  4. filtrationThe organic phase was filtered through a phase separator
  5. customevaporated

Sources & evidence

ORD record
ord-703ae0062c5d4124bd4deffc10e3b63f
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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