Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (4-Methoxyphenyl)hydrazine | HCID 77023 | — |
| Reactant | HCID 58399458 | HCID 58399458 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 53477390 | HCID 53477390 | 44.1% |
Reaction Steps
To a suspension of 4-methoxyphenylhydrazine (165 mg, 0.944 mmol) in ethanol (5.0 mL), triethylamine (258 μL, 1.88 mmol) was added, and the obtained solution was stirred at room temperature for 30 minutes. The resulting solution was added to a solution of 3-(1-hydroxycyclohexyl)-1-(4-tolyl)-2-propyn-1-one (Reference Example 14) (214 mg, 0.883 mmol) in ethanol (3.0 mL), and the resulting mixture was stirred at room temperature for 20 hours. The reaction solution was concentrated under reduced pressure, and distilled water was added to the residue. The resulting solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate) to obtain the title compound (141 mg, 0.389 mmol, 44%) as a yellow amorphous product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08247569B2 |
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| Source dataset | uspto-grants-2012_08 |
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| ORD ID | ord-2823e327f0c9422781da1afb89c9c797 |
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| Source note | uspto-grants-2012_08 |
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