Water → HCID 22931941, compound

HRID 2373338Notes

Reaction equation

HRID 2373338 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[CH3:7][CH:8]([C:13]1[CH:19]=[C:18]([C:20](F)(F)[C:21]([F:24])([F:23])[F:22])[CH:17]=[CH:16][C:14]=1[NH2:15])[CH2:9][CH:10]([CH3:12])[CH3:11].O.S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1>[CH3:7][CH:8]([C:13]1[CH:19]=[C:18]([CH2:20][C:21]([F:22])([F:24])[F:23])[CH:17]=[CH:16][C:14]=1[NH2:15])[CH2:9][CH:10]([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 22931943HCID 22931943, compound

Product 1

HCID 22931941HCID 22931941, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aluminum lithium hydride (1.62 g, 4.26 mmol) was dissolved in tetrahydrofuran (20 ml), followed by adding dropwise thereto 2-(1,3-dimethylbutyl)-4-pentafluoroethylaniline (974 mg, 3.3 mmol), and the resulting mixture was stirred at reflux temperature for 3 hours. Water was added to the reaction mixture in small portions under ice-cooling, followed by stirring for 10 minutes. Magnesium sulfate was added thereto and then stirred for 10 minutes. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure, after which the residue was separated and purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain 260 mg of the desired compound.

Workup

  1. additionby adding dropwise
  2. temperatureat reflux temperature for 3 hours
  3. temperaturecooling
  4. stirringstirred for 10 minutes
  5. filtrationThe reaction mixture was filtered through Celite
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customafter which the residue was separated
  8. custompurified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-ab18b279681c4744b41059ad8229bc13
Source dataset
uspto-grants-2008_12
Patent number
US07459477B2

Reaction notes

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