HCID 66731948, compound → HCID 66732576, compound

HRID 1963174Notes

Reaction equation

HRID 1963174 reaction equation
Cl.[Cl:2][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])=[C:5]([F:19])[CH:4]=1>CO.[Pt](=O)=O>[ClH:2].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:10][CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:16][CH2:17][NH:18]2)=[C:5]([F:19])[CH:4]=1

Participants

4

Reactant 1

HCID 66731948HCID 66731948, compound

Product 1

HCID 66732576HCID 66732576, compoundYield 201.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-(4-chloro-2-fluorophenyl)isonicotinate hydrochloride (7.26 g, 24.03 mmol) was dissolved in MeOH (100 mL) and platinum(IV) oxide (0.546 g, 2.40 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 1 h. The catalyst was filtered off and washed with MeOH and the eluate evaporated yielding methyl 2-(4-chloro-2-fluorophenyl)piperidine-4-carboxylate hydrochloride (7.45 g, quant.) as a brown solid. MS m/z 272 (M+H)+

Workup

  1. customwas hydrogenated in a Büchi hydrogenator at room temperature
  2. filtrationThe catalyst was filtered off
  3. washwashed with MeOH
  4. customthe eluate evaporated

Sources & evidence

ORD record
ord-b59e156df445492c8e0112fd8fe7454f
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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