HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethylene Glycol → N-Benzyl-3-methoxyaniline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Benzene, 1-iodo-3-methoxy- | HCID 69839 | — |
| 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 | N-Benzyl-3-methoxyaniline | HCID 9942546 | 80.2% |
Reaction Steps
The general procedure under argon was followed using copper(I) iodide (10 mg, 0.05 mmol), K3PO4 (425 mg, 2.00 mmol), benzylamine (131 μL, 1.20 mmol), 3-iodoanisole (119 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=10/1, Rf=0.4) afforded N-(3-methoxyphenyl)benzylamine (171 mg, 80% isolated yield) as white solid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Ali, M. H.; Buchwald, S. L. J. Org. Chem. 2001, 66, 2560-2565.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06867298B2 |
| Source dataset | uspto-grants-2005_03 |
| ORD ID | ord-7b00ed9fdaf549f08d4ffe8bf53a1dee |
| Source note | uspto-grants-2005_03 |