4-(4-Nitrophenyl)-1-(3,3,3-trifluoropropyl)-1,2,3,6-tetrahydropyridine → 4-[1-(3,3,3-Trifluoropropyl)piperidin-4-yl]aniline

HRID 1520035Notes

Reaction equation

HRID 1520035 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][C:18]([F:21])([F:20])[F:19])[CH2:14][CH:15]=2)=[CH:6][CH:5]=1)([O-])=O>CCOC(C)=O.[Pd]>[F:21][C:18]([F:19])([F:20])[CH2:17][CH2:16][N:13]1[CH2:14][CH2:15][CH:10]([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)[CH2:11][CH2:12]1

Participants

4

Reactant 1

HCID 679846324-(4-Nitrophenyl)-1-(3,3,3-trifluoropropyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 679811014-[1-(3,3,3-Trifluoropropyl)piperidin-4-yl]anilineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In Paar autoclave, a solution of 4-(4-nitrophenyl)-1-(3,3,3-trifluoropropyl)-1,2,3,6-tetrahydropyridine (2.6 g; 8.66 mmol; 1.0 eq.) in EtOAc (52 mL) was hydrogenated at 25 bars O/N in presence of Pd/C (moistened, 10%, 0.26 g; 2.44 mmol; 0.28 eq.). Reaction mixture was filtered through a celite pad. Filtrate was then concentrated under reduced pressure to give the title compound as a brown oil (2.33 g, 99%). UPLC/MS: (MS+) 273.4.

Workup

  1. customReaction mixture
  2. filtrationwas filtered through a celite pad
  3. concentrationFiltrate was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-ce94ca6f3019493d98416abd1a279c49
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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