HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Fluoro-3-iodobenzene → 1-[3-(3-Fluorophenyl)-2-propynyl]4-methylpiperidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Fluoro-3-iodobenzene | HCID 70725 | — |
| Reactant | 4-Methyl-1-(prop-2-yn-1-yl)piperidine | HCID 11355509 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Tri(o-toluoyl)phosphine | HCID 19696886 | — |
| Solvent | Diethylamine | HCID 8021 | — |
| Product | 1-[3-(3-Fluorophenyl)-2-propynyl]4-methylpiperidine | HCID 9899438 | 56.2% |
Reaction Steps
A mixture of 3-fluoroiodobenzene (8.88 g), 4-methyl-1-(2-propynyl)piperidine (6.80 g), palladium acetate (0.045 g), tri-o-toloylphosphine (0.24 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 the solvent was removed under reduced pressure. Distillation of the residue under reduced pressure gave an oil (5.20 g) of boiling point 105° C./0.07 mm Hg.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07084158B2 |
| Source dataset | uspto-grants-2006_08 |
| ORD ID | ord-407eb598551c4c3b88f8f45387ed5837 |
| Source note | uspto-grants-2006_08 |