Sodium Bicarbonate → HCID 22038431, compound

HRID 1790439Notes

Reaction equation

HRID 1790439 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[C:16](=O)[C:15]2=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[CH:16]=[CH:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 22038368HCID 22038368, compound

Product 1

HCID 22038431HCID 22038431, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 2 M solution (0.47 ml) of a diborane/dimethyl sulfide complex in tetrahydrofuran was added to a solution of 1-(1-benzylpiperidin-4-yl)-6-methoxyindoline-2,3-dione (110 mg) in tetrahydrofuran (2 ml) followed by stirring for 1 hr and then heating under reflux for 4.5 hr. After the completion of the reaction, an aqueous solution of sodium bicarbonate was added to the reaction solution, which was then extracted with ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate andthe solvent was removed. The residue was dissolved in pyridine and stirred for 4.5 hr. After evaporating off pyridine, ethyl acetate and an aqueous solution of sodium bicarbonate were added thereto. The ethyl acetate layer was separated and dried over magnesium sulfate. After distilling off the solvent, the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give 1-(1-benzylpiperidin-4-yl)-6-methoxyindole (28 mg) (yield: 28%).

Workup

  1. temperatureheating
  2. temperatureunder reflux for 4.5 hr
  3. customAfter the completion of the reaction
  4. extractionwas then extracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over magnesium sulfate andthe solvent
  6. customwas removed
  7. dissolutionThe residue was dissolved in pyridine
  8. stirringstirred for 4.5 hr
  9. customAfter evaporating off pyridine, ethyl acetate
  10. additionan aqueous solution of sodium bicarbonate were added
  11. customThe ethyl acetate layer was separated
  12. dry with materialdried over magnesium sulfate
  13. distillationAfter distilling off the solvent
  14. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-264b00879f70421db4e632e523b628a0
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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