HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 68912754, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Diisopropylamide | HCID 5062348 | — |
| Reactant | HCID 68535478 | HCID 68535478 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68912754 | HCID 68912754 | 23% |
Reaction Steps
Under argon, 3-benzyl-6-(2-iodobenzyl)-1,4-dimethylpiperazine-2,5-dione (polar isomer from 1.5, 100 mg, 0.22 mmol) was stirred together with diisopropylamide (0.5 ml), trimethylsilylacetylene (40 mg, 0.4 mmol), Pd(PPh3)4 (60 mg, 0.05 mmol) and CuI (10 mg, 0.05 mmol) in DMF (abs., 5 ml) at 80° C. for 12 h. After cooling and addition of H2O, the mixture was extracted with methyl tert-butyl ether and the organic phases were dried and concentrated. Purification by column chromatography gave 21 mg (23%) of the target compound as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08450301B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-f530ffc3ef6b4b75914ed0477ffae5fc |
| Source note | uspto-grants-2013_05 |