Hydrochloric Acid → Methyl 2-(3,4-difluorophenyl)piperidine-4-carboxylate hydrochloride

HRID 1963130Notes

Reaction equation

HRID 1963130 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][N:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][C:7]=1[F:8].[ClH:19]>[Pt](=O)=O>[ClH:19].[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:10][CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:16][CH2:17][NH:18]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66731610Methyl 2-(3,4-difluorophenyl)isonicotinate

Product 1

HCID 66732136Methyl 2-(3,4-difluorophenyl)piperidine-4-carboxylate hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

Methyl 2-(3,4-difluorophenyl)isonicotinate (5.821 g, 23.36 mmol) was dissolved in hydrogen chloride (1.25 M in MeOH) (37.4 mL, 46.72 mmol) and stirred at room temperature for 30 min. The solvent was evaporated in vacuo. The remaining HCl salt was redissolved in MeOH (20 mL), platinum(IV) oxide (0.159 g, 0.70 mmol) was added and the reaction mixture hydrogenated in a Büchi hydrogenator at 5 bar and room temperature for 6 h. The catalyst was filtered off, washed with MeOH and the filtrate evaporated in vacuo to yield methyl 2-(3,4-difluorophenyl)piperidine-4-carboxylate hydrochloride (6.10 g, 90%) as a pale solid. MS m/z 256 (M+H)+.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionThe remaining HCl salt was redissolved in MeOH (20 mL)
  3. waitthe reaction mixture hydrogenated in a Büchi hydrogenator at 5 bar and room temperature for 6 h
  4. filtrationThe catalyst was filtered off
  5. washwashed with MeOH
  6. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-786251ad61e245609d44a1fa48a26ced
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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