Reacción #51622

Ecuación de reacción

6,7-dimethoxy-2-quinoxaline carboxaldehyde

MeOH 1,2-dichloroethane

cyclohexylamine

NaBH4

→

Cyclohexyl-(6,7-dimethoxyquinoxalin-2-ylmethyl)-amine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction mixture is stirred overnight
2. 2
   ConcentraciónThe mixture is then concentrated
3. 3
   Otrochromatographed (50% EtOAc/hexanes—approximately 5% MeOH in 50% EtOAc/hexanes)
4. 4
   workup.DISSOLUTIONThe oil is dissolved in EtOAc/hexanes
5. 5
   workup.ADDITIONtreated with HCl in EtOH
6. 6
   ConcentraciónThe resulting solution is concentrated
7. 7
   Otrothe solids are triturated with isopropanol
8. 8
   Otroto provide a white solid
9. 9
   Otroafter drying in vacuo at 60° C. (m.p. 185-190° C., dec.)

Procedimiento

To a 0.067 M solution of 6,7-dimethoxy-2-quinoxaline carboxaldehyde in 2:1 MeOH/1,2-dichloroethane (7.5 mL, 0.5 mmol) is added cyclohexylamine (0.11 mL, 0.9 mmol). The reaction is allowed to stir at room temperature overnight, then NaBH4 (0.038 g, 1 mmol) is added and the reaction mixture is stirred overnight. The mixture is then concentrated and chromatographed (50% EtOAc/hexanes—approximately 5% MeOH in 50% EtOAc/hexanes). The oil is dissolved in EtOAc/hexanes and treated with HCl in EtOH. The resulting solution is concentrated and the solids are triturated with isopropanol to provide a white solid after drying in vacuo at 60° C. (m.p. 185-190° C., dec.). Anal. Calcd. for C17H23N3O2.HCl: C, 60.44; H, 7.16; N, 12.44; Found: C, 60.48; H, 6.88; N, 12.07.

Fuente