HuagongsheHuagongshe Chemistry Print Report · For research reference only
Morpholine → 4-(2-Methoxyphenyl)morpholine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | o-Iodoanisole | HCID 68257 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | sodium 2-methylpropan-2-olate | HCID 178418730 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-(2-Methoxyphenyl)morpholine | HCID 10655409 | 70% |
Reaction Steps
To a solution of 1-iodo-2-methoxybenzene (1 g, 4.28 mmol) in dioxane (10 mL) was added morpholine (446.8 mg, 5.12 mmol), Pd2(dba)3 (100 mg, 0.1 mmol), Xantphos (200 mg, 0.3 mmol) and t-BuONa (671 mg, 6.0 mmol). Under a N2 atmosphere the reaction mixture was heated at reflux temperature for 16 h. The solvent was then removed and the residue dissolved in ethyl acetate and washed with water. The separated organic layer was concentrated to give the crude product which was used in next step without further purification (578 mg Yield 70%). LCMS (m/z): 194.1 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09266836B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-d67385388ed2462abfb5fb117b237643 |
| Source note | uspto-grants-2016_02 |