HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 278776Generated: October 30, 2026
Trimethylsilylacetylene → Benzyl-[-(4-trimethylsilanylethynyl-phenyl)-cyclopropyl]-methylamine
https://huagongshe.com/reaction/278776
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Benzyl-[1-(4-bromophenyl)-cyclopropyl]-methylamine | HCID 22568936 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | Benzyl-[-(4-trimethylsilanylethynyl-phenyl)-cyclopropyl]-methylamine | HCID 69548036 | 85.7% |
Reaction Steps
Using General Procedure D; benzyl-[1-(4-bromophenyl)-cyclopropyl]-methylamine (Intermediate 130, 90.0 mg, 0.28 mmol) in triethylamine (8 mL) was treated with copper(I)iodide (6.0 mg, 0.03 mmol) and then sparged with argon for 5 minutes. Trimethylsilyl acetylene (0.70 g, 7.1 mmols) was then added followed by dichlorobis(triphenylphosphine)palladium(II) (20.0 mg, 0.03 mmol). The resulting reaction mixture was heated to 70° C. for 5 days. The title compound 80 mg (84%) was isolated by chromatography (0-2% EtOAc-hexanes).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06359135B1 |
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| Source dataset | uspto-grants-2002_03 |
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| ORD ID | ord-ea3814f9c9314a1487acab6272b96cfa |
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| Source note | uspto-grants-2002_03 |
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