Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 2,2,6,6-Tetramethyl-3,5-heptanedione | HCID 70700 | — |
| Reactant | 1-Bromo-4-(trifluoromethoxy)benzene | HCID 521008 | — |
| Reactant | HCID 70873672 | HCID 70873672 | — |
| Catalyst | Cupric Chloride | HCID 24014 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 70873513 | HCID 70873513 | 53.3% |
Reaction Steps
4-({1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenyl]piperidin-4-yl}methyl)phenol (1.10 g, 3.0 mmol), cesium carbonate (0.977 g, 3.0 mmol), N-methylpyrrolidinone (5 ml), 1-bromo-4-(trifluoromethoxy)benzene (0.723 g, 2.99 mmol) and dipivaloylmethane (0.3 g, 1.5 mmol) were mixed, and the atmosphere was replaced with nitrogen. Copper chloride (0.030 g, 0.3 mmol) was added thereto and stirred at 120° C. for 24 hours. An ammonium chloride aqueous solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=75:25) to afford the title compound as a colorless powder (0.84 g, 53%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09051333B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-491710ff6cde4c6c8d1782953e2ca561 |
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| Source note | uspto-grants-2015_06 |
|---|