Morpholine → 3-(3,4-Dimethoxyphenyl)-7-(2-hydroxy-3-morpholinopropoxy)-4H-chromen-4-one

HRID 1436315Notes

Reaction equation

HRID 1436315 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][C:16]([O:22][CH2:23][CH:24]4[CH2:26][O:25]4)=[CH:17][CH:18]=3)[O:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][C:16]([O:22][CH2:23][CH:24]([OH:25])[CH2:26][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[CH:17][CH:18]=3)[O:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 442271773-(3,4-Dimethoxyphenyl)-7-(oxiran-2-ylmethoxy)-4H-chromen-4-one

Product 1

HCID 442273883-(3,4-Dimethoxyphenyl)-7-(2-hydroxy-3-morpholinopropoxy)-4H-chromen-4-oneYield 52.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of compound 4 (obtained from example 2) (0.35 g, 1 mmol), morpholine (0.43 g, 5 mmol), and ethanol (30 mL) was refluxed for 6 hrs (TLC monitoring). After removal of solvent in vacuo, the residue was treated with H2O (50 mL). The resulting precipitate was collected and purified by column chromatography (MeOH/CH2Cl2=1:25) to give the title compound 6a (0.23 g, 51% yield). M.p.: 135-136° C.

Workup

  1. temperaturewas refluxed for 6 hrs (TLC monitoring)
  2. customAfter removal of solvent in vacuo
  3. additionthe residue was treated with H2O (50 mL)
  4. customThe resulting precipitate was collected
  5. custompurified by column chromatography (MeOH/CH2Cl2=1:25)

Sources & evidence

ORD record
ord-42f370e669074868be9ce5ce4d9bd421
Source dataset
uspto-grants-2009_11
Patent number
US07618998B2

Reaction notes

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