Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Iodobenzene | HCID 11575 | — |
| Reactant | L-Proline | HCID 145742 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 4-Phenylmorpholine | HCID 62339 | 44.4% |
Reaction Steps
1-iodobenzene (28.12 g, 137.84 mmol) was added to morpholine (12.0 g, 137.93 mmol). L-Proline (3.12 g, 27.13 mmol) was then added, followed by the addition of CuI (2.6 g, 13.68 mmol) and DMSO (120 mL). The resulting solution was stirred at 90° C. for 4 hours, and then the reaction mixture was then quenched by the addition of 300 mL of iced water. The resulting solution was extracted using dichloromethane (2×200 mL), and the organic layers combined, dried (Na2SO4) and concentrated. The residue was purified by column chromatography using a petroleum ether solvent system. The collected fractions were combined and concentrated to give 10 g (42%) of 4-phenylmorpholine as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07696229B2 |
|---|
| Source dataset | uspto-grants-2010_04 |
|---|
| ORD ID | ord-4164fd1b61e74a6d9f80aaaaffc40ee9 |
|---|
| Source note | uspto-grants-2010_04 |
|---|
