HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1861500Generated: November 2, 2026
Trimethylsilylacetylene → Cyclopropyl-ethyl-(2-methyl-4-trimethylsilanylethynyl-benzyl)-amine
https://huagongshe.com/reaction/1861500
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | (4-Bromo-2-methyl-benzyl)-cyclopropyl-ethyl-amine | HCID 22568961 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | Cyclopropyl-ethyl-(2-methyl-4-trimethylsilanylethynyl-benzyl)-amine | HCID 22568965 | 98.6% |
Reaction Steps
Using General Procedure D; (4-bromo-2-methyl-benzyl)-cyclopropyl-ethyl-amine (Intermediate 159, 620.0 mg, 2.31 mmols) in triethylamine (8 mL) was treated with copper(I)iodide (44.0 mg, 0.23 mmol) and then sparged with argon for 15 minutes. Trimethylsilylacetylene (1.04 g, 10.6 mmols) was then added followed by dichlorobis-(triphenylphosphine)palladium(II) (162.0 mg, 0.23 mmol). The resulting reaction mixture was heated to 70° C. for 5 days. The title compound (650.0 mg, 98%) was isolated by chromatography (1-4% EtOAc-hexanes).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06531599B2 |
|---|
| Source dataset | uspto-grants-2003_03 |
|---|
| ORD ID | ord-d50764b2dbf34fb0a26460a392e567c7 |
|---|
| Source note | uspto-grants-2003_03 |
|---|
