Methyl 2-(2,4-difluorophenyl)isonicotinate hydrochloride → Methyl 2-(2,4-difluorophenyl)piperidine-4-carboxylate hydrochloride

HRID 1963170Notes

Reaction equation

HRID 1963170 reaction equation
[ClH:1].[F: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:1].[F: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 66731571Methyl 2-(2,4-difluorophenyl)isonicotinate hydrochloride

Product 1

HCID 66731925Methyl 2-(2,4-difluorophenyl)piperidine-4-carboxylate hydrochlorideYield 58.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-(2,4-difluorophenyl)isonicotinate hydrochloride (3.93 g, 13.76 mmol) was dissolved in MeOH (40 mL) and platinum(IV) oxide (0.312 g, 1.38 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 2 h. The catalyst was filtered off, washed with MeOH and the eluate evaporated leaving methyl 2-(2,4-difluorophenyl)piperidine-4-carboxylate hydrochloride (2.34 g, 58%) as a slightly yellow solid. MS m/z 256 (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-693db4c5c9994e1eb734df785919ad95
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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