Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-Isopropylpiperazine | HCID 78013 | — |
| Reactant | 4-Bromo-2-nitroanisole | HCID 118533 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 59442053 | HCID 59442053 | 55% |
Reaction Steps
To an N2 degassed solution of 1,4-dioxane (50 mL, Aldrich) was added 4-bromo-1-(methyloxy)-2-nitrobenzene (1.0 g, 4.31 mmol, Aldrich), XANTPHOS (0.74 g, 1.28 mmol, Aldrich), Pd2(dba)3(0.79 g, 0.86 mmol, Aldrich), Cs2CO3 (2.8 g, 8.63 mmol, Aldrich), and 1-isopropylpiperazine (1.10 g, 8.6 mmol, Oakwood Chemicals). After heating overnight at 90° C., the reaction was diluted with ethyl acetate (50 mL), washed with water (50 mL), organic layer adsorbed to silica gel and purified by column chromatography (dichloromethane to 5% methanol/dichloromethane) to afford 1-(1-methylethyl)-4-[4-(methyloxy)-3-nitrophenyl]piperazine (0.66 g, 55%). ESIMS (M+H)+=280.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07981903B2 |
|---|
| Source dataset | uspto-grants-2011_07 |
|---|
| ORD ID | ord-21e40ee8c5a14311bf6ef78d612718b1 |
|---|
| Source note | uspto-grants-2011_07 |
|---|
