HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethylene Glycol → N-Methyl-N-phenylbenzylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | N-Methylbenzylamine | HCID 7669 | — |
| 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 | 1-Butanol | HCID 263 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | N-Methyl-N-phenylbenzylamine | HCID 69191 | 74% |
Reaction Steps
The general procedure under argon was followed using copper(I) iodide (19 mg, 0.10 mmol), K3PO4 (425 mg, 2.00 mmol), N-methylbenzylamine (155 μL, 1.20 mmol), iodobenzene (112 μL, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 1-butanol (1.0 mL) at 90° C. Column chromatography using a solvent mixture (hexane/ethyl acetate=20/1, Rf=0.5) afforded N-methyl-N-phenylbenzylamine (146 mg, 74% isolated yield) as colorless liquid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron 1999, 55, 12829–12842.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07115784B2 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-49b24f5bd03946389e133a8b8a2b4105 |
| Source note | uspto-grants-2006_10 |