Trifluoromethylpyridine → 2-(trifluoromethyl)piperidine

HRID 473798Notes

Reaction equation

HRID 473798 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1>C(O)(=O)C.Cl.[Pt]=O>[F:1][C:2]([F:10])([F:9])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][NH:4]1

Participants

5

Reactant 1

HCID 136199Trifluoromethylpyridine

Product 1

HCID 112636082-(trifluoromethyl)piperidine

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 2-(trifluoromethyl)pyridine (0.38 g, 2.60 mmol) and platinum oxide (0.04 g, 0.18 mmol) in acetic acid (15 mL) and concentrated hydrochloric acid (2 mL) was hydrogenated in a Parr apparatus at 40 psi for 3 d. Filtration through celite and concentration of the filtrate provided 2-(trifluoromethyl)piperidine as hydrochloride salt which was used without further purification. 1H NMR (400 MHz, methanol-d4): 4.18 (m, 1H), 3.50 (m, 1H), 3.15 (m, 1H), 2.16 (m, 1H), 1.99 (m, 2H), 1.71 (m, 3H).

Workup

  1. filtrationFiltration through celite and concentration of the filtrate

Sources & evidence

ORD record
ord-324f44cca59a41c781b1eb997589b82b
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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