HuagongsheHuagongshe Chemistry Print Report · For research reference only
Piperidine → 1-[2-(4-Trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 1-(2-(4-Iodophenoxy)ethyl)pyrrolidine | HCID 21959166 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Product | 1-[2-(4-Trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidine | HCID 67363455 | — |
Reaction Steps
Under a nitrogen atmosphere and while cooling with ice a reaction mixture of 1.5 g (4.72 mmol) 1-[2-(4-iodo-phenoxy)-ethyl]-pyrrolidine, 0.735 ml (5.2 mmol) ethynyl-trimethyl-silane, 15 mL piperidine, 115.5 mg (0.1 mmol) tetrakis-triphenylphosphane-palladium and 19 mg (0.1 mmol) CuI is stirred for 1 h. Then the reaction mixture is evaporated down, the residue is taken up in 20 mL water and extracted with EtOAc. The organic phase is dried over Na2SO4. The purification is carried out by column chromatography on silica gel (EtOAc/MeOH/NH3 95:5:0.5).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08618132B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-0de9a844d51c4d5eaf0ee3bf9f794ecd |
| Source note | uspto-grants-2013_12 |