HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dicyclohexylamine → 2-[6-[(6-Bromohexyl)oxy]-1-hexynyl]quinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dicyclohexylamine | HCID 7582 | — |
| Reactant | 2-Bromoquinoline | HCID 2762756 | — |
| Reactant | 6-[(6-Bromohexyl)oxy]-1-hexyne | HCID 21867158 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 2-[6-[(6-Bromohexyl)oxy]-1-hexynyl]quinoline | HCID 19876759 | 75.9% |
Reaction Steps
A mixture of 2-bromoquinoline (3.00 g), 6-[(6-bromohexyl)oxy]-1-hexyne (3.77 g), BTPC (90 mg), copper (I) iodide (11 mg) and dicyclohexylamine (2.79 g) in acetonitrile (35 ml) was stirred at room temperature under nitrogen for 20 h. The mixture was diluted with ether (90 ml), filtered and the filtrate evaporated in vacuo to give a brown oil. Purification by FCC eluting with hexane:ether (4:1→2:1) gave the title compound as a brown oil (4.25 g), t.l.c. (hexane:ether 2:1) Rf 0.22.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05149698 |
| Source dataset | uspto-grants-1992_09 |
| ORD ID | ord-4e36df1b6661457aa2f85e086e71baf7 |
| Source note | uspto-grants-1992_09 |