Piperazine → 3-(3,4-Dimethoxyphenyl)-7-[2-hydroxy-3-(piperazin-1-yl)propoxy]-4H-chromen-4-one

HRID 1436316Notes

Reaction equation

HRID 1436316 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][NH: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][NH: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 4837PiperazineHCID 442271773-(3,4-Dimethoxyphenyl)-7-(oxiran-2-ylmethoxy)-4H-chromen-4-one

Product 1

HCID 578301103-(3,4-Dimethoxyphenyl)-7-[2-hydroxy-3-(piperazin-1-yl)propoxy]-4H-chromen-4-oneYield 56.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of compound 4 (obtained from example 2) (0.35 g, 1 mmol), piperazine (0.43 g, 5 mmol), and ethanol (30 mL) was refluxed for 6 hrs (TLC monitoring). After removal of solvent in vaccuo, 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 6b (0.25 g, 56% yield). M.p.: 84-85° C.

Workup

  1. temperaturewas refluxed for 6 hrs (TLC monitoring)
  2. customAfter removal of solvent in vaccuo
  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-0999375f9d8e481897207884a402b33b
Source dataset
uspto-grants-2009_11
Patent number
US07618998B2

Reaction notes

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