HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethylene Glycol → N-Benzyl-3,5-dimethylaniline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 1-Iodo-3,5-dimethylbenzene | HCID 140924 | — |
| 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-3,5-dimethylaniline | HCID 10176701 | 84% |
Reaction Steps
The general procedure under argon or air was followed using copper(I) iodide (10 mg, 0.05 mmol), K3PO4 (425 mg, 2.00 mmol), benzylamine (131 μL, 1.20 mmol), 5-iodo-m-xylene (144 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=0.5) afforded 5-(N-benzyl)amino-m-xylene (177 mg, 84% isolated yield) as colorless liquid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144-1157.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09067955B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-aa48b41f7e304134bc64a94bed7bb17a |
| Source note | uspto-grants-2015_06 |