Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Allylamine | HCID 7853 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 4-Sulfanylidene-1,3-thiazolidin-2-one | HCID 1539595 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | 1-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde tosylate | HCID 86678684 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 178456915 | HCID 178456915 | 44.2% |
Reaction Steps
To a solution of 4-thioxo-1,3-thiazolidin-2-one (60 mg) in ethanol (2 mL) was added prop-2-en-1-amine (26 mg) at room temperature. The reaction mixture was stirred at room temperature for 2 hr. 1-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde tosylate (230 mg) and potassium tert-butoxide (101 mg) were added to the reaction mixture at room temperature, and the mixture was stirred at 80° C. for 3 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (95 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08772277B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-5a519cf2e9ee42e0af5572da4f41a196 |
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| Source note | uspto-grants-2014_07 |
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