Water → HCID 22038254, compound

HRID 1790408Notes

Reaction equation

HRID 1790408 reaction equation
[NH:1]([C:5]1[CH:27]=[CH:26][C:8]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[C:2]([CH3:4])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:2]([NH:1][C:5]1[CH:27]=[CH:26][C:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18]3)[CH2:15][CH2:16]2)=[CH:7][CH:6]=1)[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22038395HCID 22038395, compound

Product 1

HCID 22038254HCID 22038254, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[1-(4-Acetaminophenethyl)piperidin-4-yl]indoline (135 mg) was dissolved in tetrahydrofuran (5 ml). After adding lithium aluminum hydride (28 mg) at room temperature, the resultant mixture was heated under reflux for 2 hr. After adding water, the reaction solution was extracted with ethyl acetate. Then the organic layer was washed with brine and dried over magnesium sulfate. After evaporating the solvent, the obtained residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (40 mg) as an oil.

Workup

  1. temperatureunder reflux for 2 hr
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washThen the organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporating the solvent
  6. customthe obtained residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-92e4dcda843b4be29dd3f2eee44ed090
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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