Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | tert-Butyl piperazine-1-carboxylate | HCID 143452 | — |
| Reactant | HCID 71278900 | HCID 71278900 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 86681959 | HCID 86681959 | 65.3% |
Reaction Steps
A solution of (E)-2-[(1H-indol-3-yl)methylene]-5-hydroxy-2,3-dihydro-1H-inden-1-one (0.060 g, 0.22 mmol) in ethanol (3.0 mL) was added with 1-tert-butoxycarbonylpiperazine (0.049 g, 0.26 mmol), and 37% aqueous formaldehyde (0.020 g, 0.26 mmol), and the mixture was stirred overnight at 60° 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 tert-butyl (E)-4-({2-[(1H-indol-3-yl)methylene]-5-hydroxy-1-oxo-2,3-dihydro-1H-inden-4-yl}methyl)piperazine-1-carboxylate (0.068 g, 65%).
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-b83eb2d497d24fa8a671e770906a03d7 |
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| Source note | uspto-grants-2015_10 |
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