Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]nicotinate → Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylate

HRID 220038Notes

Reaction equation

HRID 220038 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[C:14]([CH:19]=2)[C:15]([O:17][CH3:18])=[O:16])=[CH:6][CH:5]=1>C(O)(=O)C.[Pd].[Pt](=O)=O>[F:21][C:2]([F:1])([F:20])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:11][NH:12][CH2:13][CH:14]([C:15]([O:17][CH3:18])=[O:16])[CH2:19]2)=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 58116526Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]nicotinate

Product 1

HCID 58116537Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst3×HCID 345198Adams' catalystCatalyst3×HCID 176Acetic AcidSolvent

Procedure

A solution of 9.20 g (23.4 mmol) of the compound from Example 41A in concentrated acetic acid (192 ml) was admixed with 1.94 g of palladium/carbon (10% palladium) and 2.23 g of platinum(IV) oxide. This was followed by hydrogenation under a hydrogen atmosphere at standard pressure for 6 h, then addition of another 1.00 g of palladium/carbon (10% palladium) and 2.00 g of platinum(IV) oxide, and hydrogenation under a hydrogen atmosphere at standard pressure overnight. Subsequently, a further 1.00 g of palladium/carbon (10% palladium) and 3.00 g of platinum(IV) oxide were added, and hydrogenation was effected under a hydrogen atmosphere at standard pressure for a further 24 h. The reaction solution was filtered through Celite, the filter residue was washed with methanol/water and the combined filtrates were concentrated under reduced pressure. The residue was taken up in dichloromethane and then washed with a 1 N aqueous sodium carbonate solution. The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. Yield: 6.64 g (85% of theory, purity 90%)

Workup

  1. waithydrogenation was effected under a hydrogen atmosphere at standard pressure for a further 24 h
  2. filtrationThe reaction solution was filtered through Celite
  3. washthe filter residue was washed with methanol/water
  4. concentrationthe combined filtrates were concentrated under reduced pressure
  5. washwashed with a 1 N aqueous sodium carbonate solution
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f37365b5927a4c20911c07be9c880431
Source dataset
uspto-grants-2012_06
Patent number
US08202862B2

Reaction notes

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