HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 1-[4-Nitro-3-(propan-2-yloxy)phenyl]piperidin-4-yl acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Piperidin-4-yl acetate | HCID 11252075 | — |
| Reactant | 4-Bromo-2-isopropoxy-1-nitro-benzene | HCID 22624321 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 1-[4-Nitro-3-(propan-2-yloxy)phenyl]piperidin-4-yl acetate | HCID 86697984 | 42.8% |
Reaction Steps
A mixture of 1 g of 4-bromo-1-nitro-2-(propan-2-yloxy)benzene, 1.19 g of piperidin-4-yl acetate, 5.01 g of caesium carbonate, 86 mg of palladium acetate and 334 mg of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, in 50 ml of dioxane, is refluxed for 3 hours. The mixture is diluted with ethyl acetate and water. The aqueous phase is extracted with ethyl acetate (2×). The combined organic phases are dried over magnesium sulfate and concentrated under vacuum. The residue is purified on silica, elution being carried out with cyclohexane/ethyl acetate (80/80 to 50/50), so as to give 530 mg 1-[4-nitro-3-(propan-2-yloxy)phenyl]piperidin-4-yl acetate in the form of a brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09115140B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-5daf20321b0d4519b620b7eec465cbe1 |
| Source note | uspto-grants-2015_08 |