N,N-Dimethyl-1,4-cyclohexanediamine → HCID 9887659, compound

HRID 1266137Notes

Reaction equation

HRID 1266137 reaction equation
Cl[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:10][C:9]2[C:4](=[CH:5][C:6]([O:20][CH3:21])=[C:7]([O:18][CH3:19])[CH:8]=2)[N:3]=1.[CH3:22][N:23]([CH3:31])[CH:24]1[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]1>C1(C)C=CC=CC=1>[CH3:19][O:18][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][C:6]=1[O:20][CH3:21])[N:3]=[C:2]([NH:30][CH:27]1[CH2:28][CH2:29][CH:24]([N:23]([CH3:31])[CH3:22])[CH2:25][CH2:26]1)[C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)=[N:10]2

Participants

4

Reactant 2

HCID 345823N,N-Dimethyl-1,4-cyclohexanediamineHCID 18549011HCID 18549011, compound

Product 1

HCID 9887659HCID 9887659, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-chloro-6,7-dimethoxy-3-pyridin-2-yl-quinoxaline (0.91 g) and N,N-dimethyl-cyclohexane-1,4-diamine (0.86 g) in toluene (30 mL) was refluxed under nitrogen atmosphere for 16 hours. 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 a yellow solid. This solid was recrystallized in ethyl acetate/hexane to give the product as yellow crystals (0.92 g); mp 168-171° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by flash chromatography (silica gel, 1:9 methanol/dichloromethane)
  5. customto give a yellow solid
  6. customThis solid was recrystallized in ethyl acetate/hexane

Sources & evidence

ORD record
ord-c7b7577ccecf4d808f49c3f13b668671
Source dataset
uspto-grants-2003_04
Patent number
US06548499B1

Reaction notes

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