HCID 59454390, compound → HCID 59454342, compound

HRID 1914767Notes

Reaction equation

HRID 1914767 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]([O:15][C:16]([F:19])([F:18])[F:17])=[C:12]([NH2:14])[CH:13]=2)[CH2:4][CH2:3]1>[Pd].CCO>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:9]=[CH:10][C:11]([O:15][C:16]([F:17])([F:18])[F:19])=[C:12]([NH2:14])[CH:13]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 59454390HCID 59454390, compound

Product 1

HCID 59454342HCID 59454342, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 5-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-trifluoromethoxy-phenylamine (0.3 g, 1.10 mmol), 10% Pd/C catalyst (100 mg) in EtOH (20 mL) was hydrogenated at 40 psi for 6 hours into a Parr apparatus. The mixture was filtered over a pad of celite, the solvent removed under vacuum and the crude residue purified by flash chromatography on silica gel (eluant: DCM/MeOH/NH3 95/05/005) to yield the title compound as a light brown solid (0.17 g, 56% yield).

Workup

  1. filtrationThe mixture was filtered over a pad of celite
  2. customthe solvent removed under vacuum
  3. customthe crude residue purified by flash chromatography on silica gel (eluant: DCM/MeOH/NH3 95/05/005)

Sources & evidence

ORD record
ord-93a07864ef6c493783ed5b734fe19e80
Source dataset
uspto-grants-2013_12
Patent number
US08614220B2

Reaction notes

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