Cyclohexylamine → 7-[3-(Cyclohexylamino)-2-hydroxypropoxy]-3-(3,4-dimethoxyphenyl)-4H-chromen-4-one
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]1Participants
4
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.