Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | HCID 1777704 | HCID 1777704 | — |
| Reactant | 1-[3-(Dimethylamino)propyl]piperazine | HCID 2736234 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 71279089 | HCID 71279089 | 43.4% |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09156827B2 |
|---|
| Source dataset | uspto-grants-2015_10 |
|---|
| ORD ID | ord-4f823e4b4631434cba49388d41a810c6 |
|---|
| Source note | uspto-grants-2015_10 |
|---|