Cyclohexylamine → 2-Cyclohexylamino-6,7-dimethoxyquinoxaline

HRID 23338Notes

Reaction equation

HRID 23338 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][C:6]([O:14][CH3:15])=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1.[CH:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>>[CH:16]1([NH:22][C:2]2[CH:11]=[N:10][C:9]3[C:4](=[CH:5][C:6]([O:14][CH3:15])=[C:7]([O:12][CH3:13])[CH:8]=3)[N:3]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 7965CyclohexylamineHCID 225731372-Chloro-6,7-dimethoxyquinoxaline

Product 1

HCID 225731502-Cyclohexylamino-6,7-dimethoxyquinoxalineYield 69%

Conditions

Temperature
135 °C

Procedure

To 0.3 g (1.34 mmol) of 2-chloro-6,7-dimethoxyquinoxaline is added approx. 1 mL of cyclohexylamine. The mixture is heated overnight at 105° C. and a further 10 hours at 135° C. The mix is partitioned between CH2Cl2 and saturated NaHCO3. The organic layer is dried (MgSO4) and concentrated. The resulting syrup is chromatographed (1:1 EtOAc:CH2Cl2) to provide 0.265 g of the product as a lt. brown solid in 69% yield (m.p. 188-189.5). Anal. calcd for C16H21N3O2: C, 66.88; H, 7.37; N, 14.62. Found: C, 66.82; H, 7.28; N, 14.45.

Workup

  1. customThe mix is partitioned between CH2Cl2 and saturated NaHCO3
  2. dry with materialThe organic layer is dried (MgSO4)
  3. concentrationconcentrated
  4. customThe resulting syrup is chromatographed (1:1 EtOAc:CH2Cl2)

Sources & evidence

ORD record
ord-60dc820a1ebd4013beebac37a1fde919
Source dataset
uspto-grants-2005_02
Patent number
US06852712B2

Reaction notes

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