HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethylene Glycol → Benzylaniline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | Benzylamine | HCID 7504 | — |
| 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 | Benzylaniline | HCID 66028 | 91% |
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), 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=0.6) afforded N-(phenyl)benzylamine (166 mg, 91% isolated yield) as colorless liquid. Spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Apodaca, R.; Xiao, W. Org. Lett. 2001, 3, 1745–1748.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07115784B2 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-ea7e9cba02694238830db9b478364899 |
| Source note | uspto-grants-2006_10 |