HCID 18914251, compound → HCID 18914267, compound

HRID 1292412Notes

Reaction equation

HRID 1292412 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18](=O)[C:19]([N:21]2[CH2:26][CH2:25][N:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:23][CH2:22]2)=O)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][N:21]2[CH2:22][CH2:23][N:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:25][CH2:26]2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

3

Reactant 2

HCID 18914251HCID 18914251, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18914267HCID 18914267, compoundYield 71.2%

Procedure

To a solution of 1-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]-2-(4-phenylpiperazin-1-yl)ethane-1,2-dione (57 mg in 2 mL dry tetrahydrofuran) was added 30 mg of lithium aluminum hydride and the mixture heated to reflux on an oil bath. After 1 hour the mixture was cooled and quenched by the sequential addition of 1 mL water and 4 mL ammonium hydroxide and 5 mL ethyl acetate. The mixture was filtered to remove the solids. The organic portion was washed with brine, dried over magnesium sulfate and the concentrate purified by flash chromatography on silica gel (ethyl acetate:hexane, 1:5) to give the title compound (38 mg). m/e=410 (M+1)

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. temperatureAfter 1 hour the mixture was cooled
  4. customquenched by the sequential addition of 1 mL water and 4 mL ammonium hydroxide and 5 mL ethyl acetate
  5. filtrationThe mixture was filtered
  6. customto remove the solids
  7. washThe organic portion was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customthe concentrate purified by flash chromatography on silica gel (ethyl acetate:hexane, 1:5)

Sources & evidence

ORD record
ord-277a0c6910174f9ea94678105f2b7a79
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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