Trifluoroacetic acid → 4-Benzyl-1,2,3,4-tetrahydro-N,N-dimethyl-3-oxo-2-quinoxalinecarboxamide

HRID 2269735Notes

Reaction equation

HRID 2269735 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]([C:18]([N:20]([CH3:22])[CH3:21])=[O:19])[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]([C:18]([N:20]([CH3:21])[CH3:22])=[O:19])[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 183331084-Benzyl-N,N-dimethyl-3,4-dihydro-3-oxo-2-quinoxalinecarboxamide

Product 1

HCID 183330164-Benzyl-1,2,3,4-tetrahydro-N,N-dimethyl-3-oxo-2-quinoxalinecarboxamideYield 89.9%

Procedure

4-Benzyl-N,N-dimethyl-3,4-dihydro-3-oxo-2-quinoxalinecarboxamide (1.47 g) was added and dissolved in ice-cooled trifluoroacetic acid (45 ml), to which was further added triethyl silane (4.6 ml). The reaction mixture was stirred at room temperature for 3 hours, then concentrated. The residue was dissolved in ethyl acetate and washed with 10% aqueous potassium carbonate solution, water and a saturated aqueous sodium chloride solution, then dried and concentrated. The obtained crystals were washed with IPE to obtain the entitled compound (1.33 g).

Workup

  1. dissolutiondissolved in ice-
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 10% aqueous potassium carbonate solution, water
  5. dry with materiala saturated aqueous sodium chloride solution, then dried
  6. concentrationconcentrated
  7. washThe obtained crystals were washed with IPE

Sources & evidence

ORD record
ord-5ab76b9a86134d7c881eb34d62c3a0ac
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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