Ethanol → HCID 178517138, compound

HRID 2297524Notes

Reaction equation

HRID 2297524 reaction equation
[OH:1][C:2]1[C:3]([CH2:12][CH2:13][C:14]([N:16]2[CH2:21][CH2:20][CH:19]([CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:18][CH2:17]2)=O)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:23]1([CH:22]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:19]2[CH2:18][CH2:17][N:16]([CH2:14][CH2:13][CH2:12][C:3]3[C:2]([OH:1])=[N:11][C:10]4[C:5]([N:4]=3)=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH2:21][CH2:20]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 178520525HCID 178520525, compound

Product 1

HCID 178517138HCID 178517138, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon atmosphere, 3-(3-hydroxyquinoxaline-2-yl)-1-(4-(diphenylmethyl)piperidyl)propane-1-one (700 mg) was dissolved in tetrahydrofuran (17 ml), and lithium aluminum hydride (100 mg) was added to the solution, followed by stirring the mixture overnight at room temperature and then at 60° C. for 2 hours. Ethanol and saturated aqueous sodium sulfate solution were added to the reaction mixture under cooling in ice, and the generated precipitates were removed by filtration, followed by concentrating the filtrate. The residue was purified by Chromatorex® Column for amines (ethyl acetate) to obtain 387 mg of 3-(3-(4-(diphenylmethyl)piperidyl)propyl)quinoxaline-2-ol. Yield: 57%.

Workup

  1. waitat 60° C. for 2 hours
  2. temperatureunder cooling in ice
  3. customthe generated precipitates
  4. customwere removed by filtration
  5. concentrationby concentrating the filtrate
  6. customThe residue was purified by Chromatorex® Column for amines (ethyl acetate)

Sources & evidence

ORD record
ord-e9f40423d5444b37a31f80e073dc70f5
Source dataset
uspto-grants-2002_12
Patent number
US06492364B1

Reaction notes

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