Tetrahydrofuran → 1-Acetyl-4-benzyl-2-(N,N-dimethylamino)methyl-1,2,3,4-tetrahydroquinoxaline

HRID 2269760Notes

Reaction equation

HRID 2269760 reaction equation
B.CSC.[CH2:5]([N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[C:14]([C:22]([N:24]([CH3:26])[CH3:25])=O)[C:13]1=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1C[O:31][CH2:30][CH2:29]1>>[C:30]([N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]([CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:13][CH:14]1[CH2:22][N:24]([CH3:26])[CH3:25])(=[O:31])[CH3:29]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 12423031(Dimethyl sulfide)trihydroboronHCID 183331084-Benzyl-N,N-dimethyl-3,4-dihydro-3-oxo-2-quinoxalinecarboxamide

Product 1

HCID 183331221-Acetyl-4-benzyl-2-(N,N-dimethylamino)methyl-1,2,3,4-tetrahydroquinoxaline

Conditions

Temperature
50 °C

Procedure

Borane-dimethylsulfide complex (10M-THF solution; 5 ml) was added to a THF (20 ml) solution of 4-benzyl-N,N-dimethyl-3-oxo-3,4-dihydro-2-quinoxalinecarboxamide (1.5 g). The reaction mixture was stirred at room temperature for one hour, further at 50° C. for 18 hours, then concentrated. The residue was dissolved in methanol (30 ml) and the mixture was stirred at 50° C. for 20 hours together with 6N hydrochloric acid (10 ml). The reaction mixture was concentrated, and the residue was dissolved in pyridine (10 ml). Acetic anhydride (0.5 ml) was added to the reaction mixture, which was stirred at room temperature for 5 hours. The reaction mixture was concentrated, and the residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/3) to obtain the entitled compound (0.6 g).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in methanol (30 ml)
  3. stirringthe mixture was stirred at 50° C. for 20 hours together with 6N hydrochloric acid (10 ml)
  4. concentrationThe reaction mixture was concentrated
  5. dissolutionthe residue was dissolved in pyridine (10 ml)
  6. additionAcetic anhydride (0.5 ml) was added to the reaction mixture, which
  7. stirringwas stirred at room temperature for 5 hours
  8. concentrationThe reaction mixture was concentrated
  9. customthe residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-a3b415200a524bb0b0799b624c63e5e8
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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