HuagongsheHuagongshe Chemistry Print Report · For research reference only
Oxalyl chloride → 2-Oxo-3-thiophen-2-yl-1,2-dihydro-quinoxaline-6-carbaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | 6-Hydroxymethyl-3-thiophen-2-yl-1H-quinoxalin-2-one | HCID 21083665 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 2-Oxo-3-thiophen-2-yl-1,2-dihydro-quinoxaline-6-carbaldehyde | HCID 21083645 | — |
| Product | 6-Piperidin-1-ylmethyl-3-thiophen-2-yl-1H-quinoxalin-2-one | HCID 21083672 | — |
Reaction Steps
The quinoxalin-2-one of the present example is prepared first via Swern oxidation with DMSO and (COCl)2 of 6-Hydroxymethyl-3-thiophen-2-yl-1H-quinoxalin-2-one to form 2-Oxo-3-thiophen-2-yl-1,2-dihydro-quinoxaline-6-carbaldehyde. The 6-carboxaldehyde compound then undergoes reductive amination with piperidine in acetonitrile in the presence of NaCNBH3 and acetic acid to afford, after an aqueous workup and purification, 6-Piperidin-1-ylmethyl-3-thiophen-2-yl-1H-quinoxalin-2-one.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07566719B2 |
| Source dataset | uspto-grants-2009_07 |
| ORD ID | ord-dc713b1913b2439e80a892441e712acf |
| Source note | uspto-grants-2009_07 |