N,N-Dimethyl-1,4-cyclohexanediamine → N-(6,7-Dichloro-3-pyridin-3-yl-quinoxalin-2-yl)-N',N'-dimethyl-cyclohexane-1,4-diamine

HRID 1266136Notes

Reaction equation

HRID 1266136 reaction equation
Cl[C:2]1[C:11]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:19])=[C:7]([Cl:18])[CH:8]=2)[N:3]=1.[CH3:20][N:21]([CH3:29])[CH:22]1[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]1>C1(C)C=CC=CC=1>[Cl:18][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][C:6]=1[Cl:19])[N:3]=[C:2]([NH:28][CH:25]1[CH2:26][CH2:27][CH:22]([N:21]([CH3:29])[CH3:20])[CH2:23][CH2:24]1)[C:11]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[N:10]2

Participants

4

Reactant 2

HCID 345823N,N-Dimethyl-1,4-cyclohexanediamineHCID 185490022,6,7-Trichloro-3-pyridin-3-yl-quinoxaline

Product 1

HCID 9844785N-(6,7-Dichloro-3-pyridin-3-yl-quinoxalin-2-yl)-N',N'-dimethyl-cyclohexane-1,4-diamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,6,7-trichloro-3-pyridin-3-yl-quinoxaline (1.0 g) and N,N-dimethyl-cyclohexane-1,4-diamine in toluene (25 mL) was refluxed for 24 hours. After refluxing, the reaction mixture was cooled, filtered, and concentrated under vacuum. The residue was purified by flash chromatography (silica gel, 1:9 methanol/dichloromethane) to give the product as a yellow solid (0.43 g); mp 158-161° C.

Workup

  1. temperatureAfter refluxing
  2. temperaturethe reaction mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by flash chromatography (silica gel, 1:9 methanol/dichloromethane)

Sources & evidence

ORD record
ord-9745cfac27884549886be0fb02d0cd96
Source dataset
uspto-grants-2003_04
Patent number
US06548499B1

Reaction notes

Loading…