Methyl 2-(2-fluoro-4-(trifluoromethyl)phenyl)isonicotinate hydrochloride → Methyl 2-(2-fluoro-4-(trifluoromethyl)phenyl)piperidine-4-carboxylate hydrochloride

HRID 1963220Notes

Reaction equation

HRID 1963220 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][N:22]=1)[C:16]([O:18][CH3:19])=[O:17]>CO.[Pt](=O)=O>[ClH:1].[F:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:6]=[CH:5][C:4]=1[CH:13]1[CH2:14][CH:15]([C:16]([O:18][CH3:19])=[O:17])[CH2:20][CH2:21][NH:22]1

Participants

4

Reactant 1

HCID 66732338Methyl 2-(2-fluoro-4-(trifluoromethyl)phenyl)isonicotinate hydrochloride

Product 1

HCID 66731513Methyl 2-(2-fluoro-4-(trifluoromethyl)phenyl)piperidine-4-carboxylate hydrochlorideYield 93%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-(2-fluoro-4-(trifluoromethyl)phenyl)isonicotinate hydrochloride (5.4 g, 16.09 mmol) was dissolved in MeOH (40 mL) and platinum(IV) oxide (0.365 g, 1.61 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 and washed with MeOH and the eluate evaporated yielding methyl 2-(2-fluoro-4-(trifluoromethyl)phenyl)piperidine-4-carboxylate hydro-chloride (5.1 g, 93%) as a slightly brown solid. MS m/z 306 (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-1f3ca084de8f480aa8ca7f562885537d
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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