Sodium sulfate decahydrate → HCID 18334089, compound

HRID 2269415Notes

Reaction equation

HRID 2269415 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1[CH:10]=[C:11]([CH:15]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[NH:16][CH:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=2)[CH3:18])[CH:12]=[CH:13][CH:14]=1)#[N:8].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[NH2:8][CH2:7][C:9]1[CH:10]=[C:11]([CH:15]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)[NH:16][CH:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=2)[CH3:18])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 18334213HCID 18334213, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18334089HCID 18334089, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium aluminum hydride in tetrahydrofuran (1N, 15 ml) was added to a solution of N-[(3-cyanophenyl)-(4-methoxyphenyl)methyl]-N-[1-(3,4-difluorophenyl)ethyl]amine (1.65 g) [prepared as described in step (a) above] in anhydrous tetrahydrofuran (20 ml) in an ice bath. The mixture was stirred at ambient temperature for 4 hours. Sodium sulfate decahydrate (15 g) was added to the reaction mixture and the insoluble material was removed by filtration using a Celite (trade mark) filter aid. The filtrate was concentrated by evaporation under reduced pressure. The residue was purified by chromatography through a silica gel column using 20:1 by volume mixture of methylene chloride and methanol as the eluant, to afford a mixture of diastereoisomers of the title compound (1.59 g) as a yellow oil.

Workup

  1. customthe insoluble material was removed by filtration
  2. filtrationfilter aid
  3. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  4. customThe residue was purified by chromatography through a silica gel column
  5. additionby volume mixture of methylene chloride and methanol as the eluant
  6. customto afford

Sources & evidence

ORD record
ord-58a3f1fd85504be6a0354bf98b575a0c
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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