4-(2-Bromo-5-(trifluoromethyl)phenyl)-1-methyl-1,2,3,6-tetrahydropyridine → 4-(2-Bromo-5-(trifluoromethyl)phenyl)-1-methylpiperidine

HRID 1473360Notes

Reaction equation

HRID 1473360 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH:17]=1>C(O)C.C(Cl)Cl.[Pt](=O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][C:3]=1[CH:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]1

Participants

5

Reactant 1

HCID 866874064-(2-Bromo-5-(trifluoromethyl)phenyl)-1-methyl-1,2,3,6-tetrahydropyridine

Product 1

HCID 866874074-(2-Bromo-5-(trifluoromethyl)phenyl)-1-methylpiperidineYield 2.363%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-(2-bromo-5-(trifluoromethyl)phenyl)-1-methyl-1,2,3,6-tetrahydropyridine was dissolved in 20 mL ethanol and the solution was treated with platinum (iv) oxide (0.194 g, 0.854 mmol), and was placed under 45 psi H2 for one hour. LC/MS showed product and debrominated product, so the reaction mixture was diluted with DCM, filtered through a plug of diatomaceous earth and was concentrated. Purification of the crude residue by silica gel column chromatography (0 to 97% EtOAc/heptane, 3% MeOH) gave 4-(2-bromo-5-(trifluoromethyl)phenyl)-1-methylpiperidine (0.065 g, 0.202 mmol, 2.363% yield). m/z (ESI) 322.0 (M+Na)+;

Workup

  1. filtrationfiltered through a plug of diatomaceous earth
  2. concentrationwas concentrated
  3. customPurification of the crude residue by silica gel column chromatography (0 to 97% EtOAc/heptane, 3% MeOH)

Sources & evidence

ORD record
ord-3f7f01e0cf1e442aadce7c4fff05d751
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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