1,1,1,3,3,3-Hexafluoro-2-(4-((4-(4-nitrobenzylidene)piperidin-1-yl)methyl)phenyl)propan-2-ol → HCID 86670937, compound

HRID 515280Notes

Reaction equation

HRID 515280 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][C:19](=[CH:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[H][H]>[Pd].C(OCC)(=O)C>[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][CH:19]2[CH2:18][CH2:17][N:16]([CH2:15][C:12]3[CH:13]=[CH:14][C:9]([C:3]([OH:8])([C:4]([F:7])([F:5])[F:6])[C:2]([F:1])([F:32])[F:33])=[CH:10][CH:11]=3)[CH2:21][CH2:20]2)=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 866709361,1,1,3,3,3-Hexafluoro-2-(4-((4-(4-nitrobenzylidene)piperidin-1-yl)methyl)phenyl)propan-2-olHCID 178418361HCID 178418361, compound

Product 1

HCID 86670937HCID 86670937, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of 1,1,1,3,3,3-hexafluoro-2-(4-((4-(4-nitrobenzylidene)piperidin-1-yl)methyl)phenyl)propan-2-ol (15.39 mmol, 7.3 g) and palladium on carbon (5%) (0.308 mmol, 0.328 g) in ethyl acetate was hydrogenated at 3 bar until the desired amount of hydrogen was consumed. The mixture was filtered through celite washing with ethyl acetate. The filtrate was concentrated under reduced pressure. The residue was chromatographed on silica (eluting with a gradient of dichloromethane to ethyl acetate) to give the title compound (4.3 g). MS (ESI) m/z 447.2 [M+H]+

Workup

  1. customwas consumed
  2. filtrationThe mixture was filtered
  3. washthrough celite washing with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was chromatographed on silica (
  6. washeluting with a gradient of dichloromethane to ethyl acetate)

Sources & evidence

ORD record
ord-81b62cf1718e4f91bae9aa5a527b2a49
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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