Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | tert-Butyl piperazine-1-carboxylate | HCID 143452 | — |
| Reactant | (Z)-2-[(1H-indol-3-yl)methylene]-6-hydroxy-5-phenylbenzofuran-3(2H)-one | HCID 71278748 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 86681914 | HCID 86681914 | 56.2% |
Reaction Steps
A solution of (Z)-2-[(1H-indol-3-yl)methylene]-6-hydroxy-5-phenylbenzofuran-3(2H)-one (0.035 g, 0.10 mmol) in methanol (3.0 mL) was added with 1-tert-butoxycarbonylpiperazine (0.021 g, 0.11 mmol), and 37% aqueous formaldehyde (0.011 g, 0.15 mmol), and the mixture was stirred overnight at 40° C. 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 tert-butyl (Z)-4-({2-[(1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-5-phenyl-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.031 g, 56%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09156827B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-db76faffc0194a8795cd47ee3aa6f2c7 |
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| Source note | uspto-grants-2015_10 |
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