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

HRID 1987495Notes

Reaction equation

HRID 1987495 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([CH:15]=O)[CH:7]=[N:6]2.CO.ClCCCl.[CH:23]1([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[BH4-].[Na+]>>[CH:23]1([NH:29][CH2:15][C:8]2[CH:7]=[N:6][C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 4

HCID 7965CyclohexylamineHCID 4311764Sodium borohydrideHCID 22134543HCID 22134543, compoundHCID 225731216, 7-Dimethoxy-2-quinoxaline carboxaldehyde

Product 1

HCID 22573183Cyclohexyl-(6,7-dimethoxyquinoxalin-2-ylmethyl)-amine

Procedure

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.

Workup

  1. stirringthe reaction mixture is stirred overnight
  2. concentrationThe mixture is then concentrated
  3. customchromatographed (50% EtOAc/hexanes-approximately 5% MeOH in 50% EtOAc/hexanes)
  4. dissolutionThe oil is dissolved in EtOAc/hexanes
  5. additiontreated with HCl in EtOH
  6. concentrationThe resulting solution is concentrated
  7. customthe solids are triturated with isopropanol
  8. customto provide a white solid
  9. customafter drying in vacuo at 60° C. (m.p. 185-190° C., dec.)

Sources & evidence

ORD record
ord-baf94a997a394531819f1f32af647802
Source dataset
uspto-grants-2009_06
Patent number
US07550597B2

Reaction notes

Loading…