Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Iodobenzene | HCID 11575 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | L-Proline | HCID 145742 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 1-Phenylpyrrolidine | HCID 77726 | 59.6% |
Reaction Steps
Pyrrolidine (21.6 g, 304.23 mmol), L-proline (1.12 g, 9.74 mmol), and CuI (960 mg, 5.05 mmol) were added sequentially to 1-iodobenzene (10.0 g, 49.02 mmol). DMSO (40 mL) was then added, and the resulting solution was stirred at 60° C. for 20 hours. The reaction mixture was then quenched by adding 400 mL of iced water. The resulting solution was extracted with ethyl acetate (3×150 mL), and the organic layers were combined, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using a 1:100 ethyl acetate/petroleum ether solvent system to afford 4.3 g (57%) of 1-phenylpyrrolidine as brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07696229B2 |
|---|
| Source dataset | uspto-grants-2010_04 |
|---|
| ORD ID | ord-a24edf014d2a41488f03db31dc34e41c |
|---|
| Source note | uspto-grants-2010_04 |
|---|
