HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Oxalyl chloride → 2-Oxo-3-thiophen-2-yl-1,2-dihydro-quinoxaline-6-carbaldehyde
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Oxalyl chloride | HCID 65578 | — |
| Edukt | 6-Hydroxymethyl-3-thiophen-2-yl-1H-quinoxalin-2-one | HCID 21083665 | — |
| Lösungsmittel | Dimethyl Sulfoxide | HCID 679 | — |
| Produkt | 2-Oxo-3-thiophen-2-yl-1,2-dihydro-quinoxaline-6-carbaldehyde | HCID 21083645 | — |
| Produkt | 6-Piperidin-1-ylmethyl-3-thiophen-2-yl-1H-quinoxalin-2-one | HCID 21083672 | — |
Reaktionsschritte
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.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08236807B2 |
| Quelldatensatz | uspto-grants-2012_08 |
| ORD ID | ord-33235b909b014dd1a0f6971bd1dcdb45 |
| Quellennotiz | uspto-grants-2012_08 |