Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 11959533 | HCID 11959533 | — |
| Catalyst | Tetrabutylammonium hydrogen sulfate | HCID 94433 | — |
| Product | HCID 86695294 | HCID 86695294 | — |
Reaction Steps
61.00 g (0.295 mol) of 1-(4-fluorobenzyl)-4-piperidone crude product was added to a reaction bottle, to which 260 mL of toluene was added. The reaction was heated and stirred at 80° C. in an oil bath, and to the reaction 70.00 g (0.318 mol) of trimethylsulfoxide iodide and 2.70 g (0.0080 mol) of tetrabutylammonium hydrogen sulfate were added in sequence, then 28.00 g (0.700 mol) sodium hydroxide dissolved in 120 mL of aqueous solution was added dropwise under stirring. After the addition, the reaction was continuously stirred at 80° C. bath temperature overnight. On the next day, the reaction was cooled, washed with water twice, extracted with a small amount of toluene, combined and dried, and the solvent was recovered to obtain light yellow liquid, 47.50 g (72.8%), i.e., a crude target product, 1H-NMR (CDCl3, ppm) δ: 7.298 (2H, m), 7.007 (2H, m), 3.519 (2H, s), 2.565 (2H, s), 2.559 (4H, m), 1.827 (2H, m), 1.534 (2H, m).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08921563B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-0b70b13b7ed94abca587b66231ba2716 |
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| Source note | uspto-grants-2014_12 |
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