Hydrochloric Acid → HCID 66732599, compound

HRID 1963181Notes

Reaction equation

HRID 1963181 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][N:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=1[F:18].Cl>CO.[Pt](=O)=O>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH:10]([C:11]([O:13][CH3:14])=[O:12])[CH2:15][CH2:16][NH:17]2)=[CH:4][C:3]=1[F:18]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66731831HCID 66731831, compound

Product 1

HCID 66732599HCID 66732599, compoundYield 192%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 887MethanolSolvent

Procedure

Methyl 2-(4-chloro-3-fluorophenyl)isonicotinate (1.473 g, 5.54 mmol) was suspended in MeOH (30 mL) and hydrogen chloride (1.25 M in MeOH, 9.86 mL, 11.09 mmol) was added dropwise during stirring. The solvent was evaporated after 15 min and the HCl salt redissolved in MeOH (10 mL) and platinum(IV) oxide (0.063 g, 0.28 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 1.5 h. Platinum(IV) oxide (0.038 g, 0.17 mmol) was added and the hydrogenation continued for 1 h. The catalyst was filtered off and washed with MeOH. The solvent was evaporated in vacuo yielding methyl 2-(4-chloro-3-fluorophenyl)piperidine-4-carboxylate hydrochloride (1.639 g, 96%) as a white solid. MS m/z 272 (M+H)+

Workup

  1. customThe solvent was evaporated after 15 min
  2. dissolutionthe HCl salt redissolved in MeOH (10 mL)
  3. customwas hydrogenated in a Büchi hydrogenator at room temperature
  4. waitthe hydrogenation continued for 1 h
  5. filtrationThe catalyst was filtered off
  6. washwashed with MeOH
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-fc61e963d7414631b6d94eed15a7df31
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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