HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 51772Generated: October 30, 2026
Trimethylsilylacetylene → Propyl-[1-(4-trimethylsilanylethynylphenyl)-cyclopropyl]-amine
https://huagongshe.com/reaction/51772
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | [1-(4-Bromophenyl)-cyclopropyl]-propylamine | HCID 22568814 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | Propyl-[1-(4-trimethylsilanylethynylphenyl)-cyclopropyl]-amine | HCID 22568956 | 75.6% |
Reaction Steps
Using General Procedure D; [1-(4-bromophenyl)-cyclopropyl]-propylamine (Intermediate 118, 100.0 mg, 0.39 mmol) in triethylamine (8 mL) was treated with copper(1)iodide (13.0 mg, 0.06 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) (48.0 mg, 0.06 mmol). The resulting reaction mixture was heated to 70° C. for 5 days. The title compound (80.0 mg, 75%) was isolated by chromatography (0-10% EtOAc-hexanes) as an orange oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06713647B2 |
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| Source dataset | uspto-grants-2004_03 |
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| ORD ID | ord-daf258c2f6f24e8bbefa64155f6de9e4 |
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| Source note | uspto-grants-2004_03 |
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