Cyclohexylamine → 7-[3-(Cyclohexylamino)-2-hydroxypropoxy]-3-(3,4-dimethoxyphenyl)-4H-chromen-4-one

HRID 1436317Notes

Reaction equation

HRID 1436317 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].[CH:27]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C(O)C>[CH:27]1([NH:33][CH2:26][CH:24]([OH:25])[CH2:23][O:22][C:16]2[CH:15]=[C:14]3[C:19]([C:20](=[O:21])[C:11]([C:5]4[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=4)=[CH:12][O:13]3)=[CH:18][CH:17]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 442271773-(3,4-Dimethoxyphenyl)-7-(oxiran-2-ylmethoxy)-4H-chromen-4-one

Product 1

HCID 442271787-[3-(Cyclohexylamino)-2-hydroxypropoxy]-3-(3,4-dimethoxyphenyl)-4H-chromen-4-oneYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of compound 4 (obtained from example 2) (0.35 g, 1 mmol), cyclohexylamine (0.50 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 6c (0.24 g, 54% yield). M.p.: 70-71° 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-53f11a9b6914488a8e59436e57e4abf5
Source dataset
uspto-grants-2009_11
Patent number
US07618998B2

Reaction notes

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