Hydrochloric Acid → Methyl 2-(2-fluoro-4-(trifluoromethoxy)phenyl)piperidine-4-carboxylate hydrochloride

HRID 1963193Notes

Reaction equation

HRID 1963193 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][N:22]=1)[C:16]([O:18][CH3:19])=[O:17].[ClH:23]>CO.[Pt](=O)=O>[ClH:23].[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[CH:13]1[CH2:14][CH:15]([C:16]([O:18][CH3:19])=[O:17])[CH2:20][CH2:21][NH:22]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66731729Methyl 2-(2-fluoro-4-(trifluoromethoxy)phenyl)isonicotinate

Product 1

HCID 66732336Methyl 2-(2-fluoro-4-(trifluoromethoxy)phenyl)piperidine-4-carboxylate hydrochlorideYield 98%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-(2-fluoro-4-(trifluoromethoxy)phenyl)isonicotinate (4.47 g, 14.18 mmol) was dissolved in methanol and hydrogen chloride (1.25 M in methanol, 17.02 mL, 21.27 mmol) was added. The solvent was evaporated and the residue redissolved in methanol (50 mL). Platinum(IV) oxide (0.322 g, 1.42 mmol) was added and the mixture hydrogenated at 5 bar at room temperature for 5 h. The catalyst was filtered off and the solvent was evaporated. Crude methyl 2-(2-fluoro-4-(trifluoromethoxy)phenyl)piperidine-4-carboxylate hydrochloride (4.97 g, 98%) was obtained as a colorless solid. MS m/z 322 (M+H)+

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue redissolved in methanol (50 mL)
  3. filtrationThe catalyst was filtered off
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d134c9a9cb79472e8475edba59546467
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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