HCID 66731664, compound → HCID 66731612, compound

HRID 1963178Notes

Reaction equation

HRID 1963178 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][N:19]=1)[C:13]([O:15][CH3:16])=[O:14]>CO.[Pt](=O)=O>[ClH:2].[Cl:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[CH:10]1[CH2:11][CH:12]([C:13]([O:15][CH3:16])=[O:14])[CH2:17][CH2:18][NH:19]1

Participants

4

Reactant 1

HCID 66731664HCID 66731664, compound

Product 1

HCID 66731612HCID 66731612, compoundYield 200.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 887MethanolSolvent

Procedure

Methyl 2-(2-chloro-4-fluorophenyl)isonicotinate hydrochloride (2.35 g, 7.78 mmol) was dissolved in methanol (50 mL) and platinum(IV) oxide (0.177 g, 0.78 mmol) was added. The reaction mixture was hydrogenated in a Büchi hydrogenator at 5 bar and room temperature for 9 h. The catalyst was removed by filtration and the solvent was evaporated. The residue was dissolved in methanol (50.0 mL) and platinum(IV) oxide (144 mg, 0.63 mmol) was added. Hydrogenation was continued at 5 bar and room temperature for 4 h. The catalyst was removed by filtration and the solvent was evaporated. Crude methyl 2-(2-chloro-4-fluorophenyl)piperidine-4-carboxylate hydrochloride (2.4 g, 100%) was obtained as a yellow solid. MS m/z 272 (M+H)+

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in methanol (50.0 mL)
  4. waitHydrogenation was continued at 5 bar and room temperature for 4 h
  5. customThe catalyst was removed by filtration
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-efe846928ed74fc89d11b358ff491dc9
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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