Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | 4-Phenylpiperidin-4-ol | HCID 96387 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 3-(3-Chloropropyl)-6-fluorobenzo[d]isoxazole | HCID 10910880 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 13207817 | HCID 13207817 | 25% |
Reaction Steps
To 50 ml of dry dimethylformamide was added, 6.0 g of 4-hydroxy-4-phenylpiperidine, 8.0 g of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole, 13.0 g of sodium bicarbonate, and a few crystals of potassium iodide. After stirring at 80° C. for one hr, the mixture was cooled, filtered, and the filtrate evaporated to an oil. The oil was stirred with 100 ml water for five mins, and then extracted with ether/ethyl acetate. The organic layer was washed with water (2×), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solvents were evaporated. Trituration with ether gave 3.0 g (25%) of product, mp 133°-137° C. Recrystallization twice from ethyl ether gave the analytical sample, mp 138°-139° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04416887 |
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| Source dataset | uspto-grants-1983_11 |
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| ORD ID | ord-d75a3a8b30e543ed8d3ca53ce6f2b516 |
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| Source note | uspto-grants-1983_11 |
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