Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Acetylcyclohexanone | HCID 13400 | — |
| Reactant | 2-Pyridineethanamine | HCID 75919 | — |
| Reactant | 4-Iodo-1,2-dimethylbenzene | HCID 141646 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58007530 | HCID 58007530 | 31.6% |
Reaction Steps
A dried flask was charged with 21 mg (0.11 mmol) CuI and 1.4 g (4.3 mmol) cesium carbonate under argon. 0.31 g (2.6 mmol) 2-pyridin-2-yl-ethylamine (CAS: 2706-56-1), 0.5 g (2.1 mmol) 4-iodo-0-xylene in solution in 1 mL dried DMF and finally 0.058 mL (0.43 mmol) 2-acetylcyclohexanone were successively added. The mixture was stirred at room temperature for 17 hours and then in a 65° C. oil-bath for 7 hours. The mixture was diluted with water. The aqueous layer was extracted twice with ethyl acetate. The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide 0.15 g (31%) of the title compound as a yellow oil. MS (m/e): 227.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08133909B2 |
|---|
| Source dataset | uspto-grants-2012_03 |
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| ORD ID | ord-9417b52f0ce4465a8d8a80ac2b0a7221 |
|---|
| Source note | uspto-grants-2012_03 |
|---|
