Dimethylamine, hydrochloride → 4-Benzyl-N,N-dimethyl-3,4-dihydro-3-oxo-2-quinoxalinecarboxamide

HRID 2269734Notes

Reaction equation

HRID 2269734 reaction equation
Cl.[CH3:2][NH:3][CH3:4].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH2:26]([N:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:36]=[C:35]([C:43]([OH:45])=O)[C:34]1=[O:46])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1.C(#N)C.C(N(CC)CC)C>[CH2:26]([N:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:36]=[C:35]([C:43]([N:3]([CH3:4])[CH3:2])=[O:45])[C:34]1=[O:46])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

8

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 154617741-Benzyl-1,2-dihydro-2-oxoquinoxaline-3-carboxylic acid

Product 1

HCID 183331084-Benzyl-N,N-dimethyl-3,4-dihydro-3-oxo-2-quinoxalinecarboxamideYield 89.4%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

Dimethylamine hydrochloride (0.57 g), WSC (1.33 g) and HOBt (0.86 g) were added to a mixed solution of 4-benzyl-3,4-dihydro-3-oxo-2-quinoxalinecarboxylic acid (1.5 g) in THF (30 ml) and acetonitrile (30 ml), to which was added dropwise triethylamine (2.3 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 15 hours. The precipitated insoluble substances were removed by filtration and the filtrate was concentrated. Water was added to the precipitate, which was extracted with ethyl acetate. The ethyl acetate layer was washed with 1N hydrochloric acid, water, a saturated aqueous sodium hydrogencarbonate solution, and a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was recrystallized from ethyl acetate-hexane to obtain the entitled compound (1.47 g).

Workup

  1. temperaturecooling
  2. customThe precipitated insoluble substances were removed by filtration
  3. concentrationthe filtrate was concentrated
  4. additionWater was added to the precipitate, which
  5. extractionwas extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with 1N hydrochloric acid, water
  7. dry with materiala saturated aqueous sodium hydrogencarbonate solution, and a saturated aqueous sodium chloride solution, then dried
  8. concentrationconcentrated
  9. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-f79e5589dc4444f9bd6676db2497efb7
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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