Formaldehyde → HCID 71279089, compound

HRID 1749697Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1.[CH3:22][N:23]([CH3:33])[CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.[CH2:34]=O>C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[C:20]([CH2:34][N:30]4[CH2:29][CH2:28][N:27]([CH2:26][CH2:25][CH2:24][N:23]([CH3:22])[CH3:33])[CH2:32][CH2:31]4)=[C:19]([OH:21])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

The synthesis was performed with reference to the known literature (Heterocycles, Vol. 53, p. 197, 2000). A solution of (Z)-2-[(1H-indol-3-yl)methylene]-6-hydroxybenzofuran-3(2H)-one (0.028 g, 0.10 mmol) in ethanol (2.0 mL) was added with 1-[3-(dimethylamino)propyl]piperazine (0.022 g, 0.13 mmol), and 37% aqueous formaldehyde (0.011 g, 0.13 mmol), and the mixture was stirred overnight at 80° C. in a sealed tube. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10)) to obtain (Z)-2-[(1H-indol-3-yl)methylene]-7-({4-[3-(dimethylamino)propyl]piperazin-1-yl}methyl)-6-hydroxybenzofuran-3(2H)-one (0.020 g, 43%).

Workup

customThe solvent was evaporated under reduced pressure
washthe residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10))

Sources & evidence

ORD record: ord-4f823e4b4631434cba49388d41a810c6
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

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