HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethylene Glycol → 4-Phenylmorpholine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Iodobenzene | HCID 11575 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | 4-Phenylmorpholine | HCID 62339 | 76% |
Reaction Steps
The general procedure under argon was followed using copper(I) iodide (10 mg, 0.05 mmol), K3PO4 (425 mg, 2.00 mmol), morpholine (130 μL, 1.50 mmol), iodobenzene (112 μL, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL). Column chromatography using a solvent mixture (hexane/ethyl acetate=20/1, Rf=0.2) afforded N-(phenyl)morpholine (124 mg, 76% isolated yield) as colorless liquid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Desmarets, C.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2000, 41, 2875-2879.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09067955B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-53f0aedc1ddf4a54ad0d1be6d26ae524 |
| Source note | uspto-grants-2015_06 |