HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetamide → HCID 57675010, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetamide | HCID 178 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | tert-Butyl 4-(4-bromobenzene-1-sulfonyl)piperidine-1-carboxylate | HCID 10949472 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 57675010 | HCID 57675010 | 82.2% |
Reaction Steps
A mixture of 4-(4-bromo-benzenesulfonyl)-piperidine-1-carboxylic acid tert-butyl ester (4 g, 9.92 mmol), acetamide (0.88 g, 14.9 mmol), Pd2(dba)3 (0.46 g, 0.49 mmol), Xantphos (0.56 g, 0.99 mmol) and cesium carbonate (9.7 g, 29.8 mmol) were suspended in dioxane (60 mL) and heated at reflux under the argon atmosphere for 4 h. The reaction mixture was cooled to room temperature and poured onto ice. Resulting yellow solids collected by filtration and dried. Crude product was purified by flash chromatography on silica gel to afford the title compound as a beige solid (3.12 g, 82%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07528143B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-6cb5445e80c7407d84302c115a881565 |
| Source note | uspto-grants-2009_05 |