7-(2,3-Epoxypropoxy)flavone → 7-[3-[N-benzyl,N-(3-nicotinylpropyl)amino]-2-hydroxypropoxy]flavone

HRID 478084Notes

Reaction equation

[O:1]1[CH2:22][CH:2]1[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:21])[CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:12]2)=[CH:7][CH:6]=1.[CH2:23]([CH2:30][CH2:31][CH2:32][NH:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=1>C(O)C>[CH2:34]([N:33]([CH2:22][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:21])[CH:10]=[C:11]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[O:12]2)=[CH:7][CH:6]=1)[CH2:32][CH2:31][CH2:30][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 7-(2,3-epoxypropoxy)flavone (15 g, 51.0 mmol) and N-(3-nicotinylpropyl)benzylamine (22.5 g, 100 mmol) in ethanol (150 ml) was heated at 60° C. for 3 hours. The ethanol was then evaporated and the residue was washed with cyclohexane (three times) to remove the excess amine. The remaining residue was then extracted with ethyl acetate (twice), and the extracts were evaporated to give a red syrup. Purification of the red syrup by flash column chromatography eluting with EtOAc--MeOH (20:1) gave 8.0 g of a yellow syrup, 30% yield, which is stored in the refrigerator and used for the further reaction.

Workup

customThe ethanol was then evaporated
washthe residue was washed with cyclohexane (three times)
customto remove the excess amine
extractionThe remaining residue was then extracted with ethyl acetate (twice), and the extracts
customwere evaporated
customto give a red syrup
customPurification of the red syrup by flash column chromatography
washeluting with EtOAc--MeOH (20:1)

Sources & evidence

ORD record: ord-8965a08bce88412b997b4a44c7a230f3
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04889941

Reaction notes

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