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

HRID 1963216Notes

Reaction equation

HRID 1963216 reaction equation
[ClH:1].[CH3:2][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].[CH3:2][C:3]1[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[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 66731728Methyl 2-(2-methyl-4-(trifluoromethyl)phenyl)isonicotinate hydrochloride

Product 1

HCID 66732222Methyl 2-(2-methyl-4-(trifluoromethyl)phenyl)piperidine-4-carboxylate hydrochlorideYield 87.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-(2-methyl-4-(trifluoromethyl)phenyl)isonicotinate hydrochloride (9 g, 27.13 mmol) was dissolved in MeOH (50 mL), platinum(IV) oxide (0.185 g, 0.81 mmol) was added and the resulting mixture hydrogenated in a Büchi hydrogenator at 5 bar for 5 h. The catalyst was filtered off and the filtrate evaporated to give methyl 2-(2-methyl-4-(trifluoromethyl)phenyl)-piperidine-4-carboxylate hydrochloride (8 g, 87%) as a yellowish solid. MS m/z 302 (M+H)+

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-dd0b37e3fc5144fe9fe74b7c75faec35
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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