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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1916755Generated: November 2, 2026

Piperidine → 1-[2-(4-Trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidine

https://huagongshe.com/reaction/1916755

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPiperidineHCID 8082—
ReactantTrimethylsilylacetyleneHCID 66111—
Reactant1-(2-(4-Iodophenoxy)ethyl)pyrrolidineHCID 21959166—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
Product1-[2-(4-Trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidineHCID 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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08618132B2
Source datasetuspto-grants-2013_12
ORD IDord-0de9a844d51c4d5eaf0ee3bf9f794ecd
Source noteuspto-grants-2013_12