HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Iodotoluene → 1-(3-o-Tolyl-2-propynyl)piperidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Iodotoluene | HCID 5128 | — |
| Reactant | 1-(Prop-2-yn-1-yl)piperidine | HCID 336652 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418903 | HCID 178418903 | — |
| Solvent | Diethylamine | HCID 8021 | — |
| Product | 1-(3-o-Tolyl-2-propynyl)piperidine | HCID 12056783 | 62.3% |
Reaction Steps
A mixture of 2-iodotoluene (6.54 g), N-(2-propynyl)piperidine (3.69 g), dichlorobis(triphenylphosphino)palladium(II) (0.05 g) and copper(I) iodide (0.1 g) in dry diethylamine (50 ml) was heated under reflux for 5 hours. The solvent was removed under reduced pressure and the residue was taken up in diethyl ether and washed with water. The organic phase was dried over magnesium sulfate and concentrated completely under reduced pressure. Distillation of the residue under reduced pressure gave 3.98 g of an oil of boiling point 96–98° C./0.08 mm Hg.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07084158B2 |
| Source dataset | uspto-grants-2006_08 |
| ORD ID | ord-0f8d0671097c4c1fb7b5e5e1778ceb8b |
| Source note | uspto-grants-2006_08 |