Hydrochloric Acid → Methyl 2-(3-fluoro-4-(trifluoromethyl)phenyl)-piperidine-4-carboxylate hydrochloride

HRID 1963224Notes

Reaction equation

HRID 1963224 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][N:21]=2)[C:15]([O:17][CH3:18])=[O:16])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[ClH:22]>CO.[Pt](=O)=O>[ClH:22].[F:1][C:2]1[CH:3]=[C:4]([CH:12]2[CH2:13][CH:14]([C:15]([O:17][CH3:18])=[O:16])[CH2:19][CH2:20][NH:21]2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:9])[F:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66732503Methyl 2-(3-fluoro-4-(trifluoromethyl)phenyl)isonicotinate

Product 1

HCID 66731714Methyl 2-(3-fluoro-4-(trifluoromethyl)phenyl)-piperidine-4-carboxylate hydrochlorideYield 94.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-(3-fluoro-4-(trifluoromethyl)phenyl)isonicotinate (2.9 g, 9.69 mmol) was dissolved in methanol and hydrogen chloride (1.25 M in methanol, 11.63 mL, 14.54 mmol) was added. The solvent was evaporated and the residue redissolved in methanol (50 mL), platinum(IV) oxide (0.220 g, 0.97 mmol) was added and the reaction mixture was hydrogenated at 5 bar and room temperature in a Büchi hydrogenator for 2 h. The catalyst was removed by filtration and the solvent was evaporated to yield methyl 2-(3-fluoro-4-(trifluoromethyl)phenyl)-piperidine-4-carboxylate hydrochloride (3.12 g, 94%). MS m/z 306 (M+H)+

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue redissolved in methanol (50 mL)
  3. customThe catalyst was removed by filtration
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2e45d39a148d4ddeacffba172e687c9a
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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