Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Piperidin-4-ol | HCID 79341 | — |
| Reactant | HCID 1777704 | HCID 1777704 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 71278638 | HCID 71278638 | 48.4% |
Reaction Steps
A solution of (Z)-2-[(1H-indol-3-yl)methylene]-6-hydroxybenzofuran-3(2H)-one (0.050 g, 0.18 mmol) obtained in Example A1, Step 1 in ethanol (2.0 mL) was added with 4-hydroxypiperidine (0.024 g, 0.22 mmol), and 37% aqueous formaldehyde (0.020 g, 0.24 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]-6-hydroxy-7-[(4-hydroxypiperidin-1-yl)methyl]benzofuran-3(2H)-one (0.034 g, 48%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09156827B2 |
|---|
| Source dataset | uspto-grants-2015_10 |
|---|
| ORD ID | ord-a75cf184298d4382aaf21bb17c355d97 |
|---|
| Source note | uspto-grants-2015_10 |
|---|