Benzylamine → N-benzyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]-2-nitroaniline

HRID 524373Notes

Reaction equation

HRID 524373 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].F[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:31]=[C:30]3[C:25]([N:26]=[CH:27][C:28]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[N:29]3)=[CH:24][CH:23]=2)=[CH:18][C:17]=1[N+:38]([O-:40])=[O:39]>CN(C=O)C.CCOC(C)=O>[CH2:1]([NH:8][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:31]=[C:30]3[C:25](=[CH:24][CH:23]=2)[N:26]=[CH:27][C:28]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[N:29]3)=[CH:18][C:17]=1[N+:38]([O-:40])=[O:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 670349977-(4-Fluoro-3-nitrophenyl)-2-(morpholin-4-yl)quinoxalin

Product 1

HCID 67035007N-benzyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]-2-nitroanilineYield 94.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzylamine (336 mg, 3.1 mmol) and potassium carbonate (865 mg, 6.2 mmol) were added to a solution of 7-(4-fluoro-3-nitrophenyl)-2-(morpholin-4-yl)quinoxalin (1.1 g, 3.1 mmol) in DMF (100 mL). The mixture was stirred 24 h at room temperature and then diluted with EtOAc. The organic phase was washed with water and saturated aqueous sodium chloride solution, then dried over sodium sulphate. After filtration and subsequent removal of solvent, the residue was purified by chromatography (silica gel, Hexane/EtOAc: 20%->100% EtOAc) giving rise to 1.29 g (93%) of the desired product.

Workup

  1. washThe organic phase was washed with water and saturated aqueous sodium chloride solution
  2. dry with materialdried over sodium sulphate
  3. filtrationAfter filtration and subsequent removal of solvent
  4. customthe residue was purified by chromatography (silica gel, Hexane/EtOAc: 20%->100% EtOAc)

Sources & evidence

ORD record
ord-e4642b30c37e4205b8a28f1073c1f7fb
Source dataset
uspto-grants-2016_05
Patent number
US09340528B2

Reaction notes

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