Oxalyl chloride → 2-Oxo-3-thiophen-2-yl-1,2-dihydro-quinoxaline-6-carbaldehyde

HRID 2220884Notes

Reaction equation

HRID 2220884 reaction equation
[C:1](Cl)([C:3](Cl)=O)=O.[OH:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[C:13]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)=[N:12]2>CS(C)=O>[N:12]1([CH2:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[C:13]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)=[N:12]3)[CH2:3][CH2:1][CH2:9][CH2:10][CH2:11]1.[O:19]=[C:14]1[C:13]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)=[N:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([CH:8]=[O:7])[CH:10]=2)[NH:15]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 210836656-Hydroxymethyl-3-thiophen-2-yl-1H-quinoxalin-2-one

Product 2

HCID 210836452-Oxo-3-thiophen-2-yl-1,2-dihydro-quinoxaline-6-carbaldehydeHCID 210836726-Piperidin-1-ylmethyl-3-thiophen-2-yl-1H-quinoxalin-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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.

Sources & evidence

ORD record
ord-78ce26a6e57d4259850b01f62f92eb8b
Source dataset
uspto-grants-2008_05
Patent number
US07368452B2

Reaction notes

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