Methanol → HCID 24960989, compound

HRID 1694653Notes

Reaction equation

HRID 1694653 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.[CH:18]1[C:23]([C:24]2[C:29](=[O:30])[C:28]3[CH:31]=[CH:32][C:33]([OH:35])=[CH:34][C:27]=3[O:26][CH:25]=2)=[CH:22][CH:21]=[C:20]([OH:36])[CH:19]=1.[OH-].[K+].CO>CC(C)=O>[OH:36][C:20]1[CH:21]=[CH:22][C:23]([C:24]2[C:29](=[O:30])[C:28]3[C:27](=[CH:34][C:33]([O:35][CH2:2][CH2:3][N:4]4[CH2:9][CH2:8][N:7]([C:10]5[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=5)[CH2:6][CH2:5]4)=[CH:32][CH:31]=3)[O:26][CH:25]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 4741833HCID 4741833, compoundHCID 5281708Daidzein

Product 1

HCID 24960989HCID 24960989, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-[4-(2-chloroethyl)piperazinyl]-4-methoxybenzene (0.929 mmol) and 4,7-dihydroxyisoflavone (0,929 mmol) in acetone (10 ml)was added 11% potassium hydroxide (0.5 ml), and the mixture stirred at reflux temperature for 48 hours. Sufficient methanol was added to precipitate unreacted starting material, which was filtered off, and solvent was removed from the filtrate under reduced pressure. The residue was purified by biotage column chromatography, eluting with 5% methanol/methylene chloride, to provide pure 3-(4-hydroxyphenyl)-7-{2-[4-(4-methoxyphenyl)piperazinyl]ethoxy}chromen-4-one.

Workup

  1. temperatureat reflux temperature for 48 hours
  2. customto precipitate unreacted
  3. filtrationwas filtered off
  4. customsolvent was removed from the filtrate under reduced pressure
  5. customThe residue was purified by biotage column chromatography
  6. washeluting with 5% methanol/methylene chloride

Sources & evidence

ORD record
ord-61cc0cbe325b4f5580cb7d283ad44eaf
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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