HuagongsheHuagongshe Chemistry Print Report · For research reference only
Formaldehyde → 7-[(cis-3,5-dimethylpiperazin-1-yl)methyl]-6-hydroxybenzofuran-3(2H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | 6-Hydroxy-3-coumaranone | HCID 235717 | — |
| Reactant | rel-(2R,6S)-2,6-dimethylpiperazine | HCID 6950261 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 7-[(cis-3,5-dimethylpiperazin-1-yl)methyl]-6-hydroxybenzofuran-3(2H)-one | HCID 71278697 | 31.3% |
Reaction Steps
A solution of 6-hydroxybenzofuran-3(2H)-one (0.300 g, 2.00 mmol) in ethanol (2 mL) was added with cis-3,5-dimethylpiperazine (0.288 g, 2.00 mmol), and 37% aqueous formaldehyde (0.162 g, 2.00 mmol) at room temperature. The reaction mixture was stirred overnight at room temperature, and then concentrated. The resulting solid was dissolved in ethyl acetate, and the precipitated solid was removed by filtration. The filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain 7-[(cis-3,5-dimethylpiperazin-1-yl)methyl]-6-hydroxybenzofuran-3(2H)-one (0.173 g, 31%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09156827B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-4528504b84a640b5996ecf1f7b7a3f6b |
| Source note | uspto-grants-2015_10 |