Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | 1,3-Propanediamine, N1,N1,N3-trimethyl- | HCID 78302 | — |
| Reactant | HCID 1777704 | HCID 1777704 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 71278620 | HCID 71278620 | 54% |
Reaction Steps
A solution of (Z)-2-[(1H-indol-3-yl)methylene]-6-hydroxybenzofuran-3(2H)-one (0.030 g, 0.11 mmol) obtained in Example A1, Step 1 in ethanol (2.0 mL) was added with N,N,N′-trimethylpropane-1,3-diamine (0.015 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-({[3-(dimethylamino)propyl](methyl)amino}methyl)-6-hydroxybenzofuran-3(2H)-one (0.024 g, 54%).
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-6ddb9d7f13a649c6a0dcb173d023a047 |
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| Source note | uspto-grants-2015_10 |
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