6-(Dimethylamino)hexylamine → N'-(6,7-Dichloro-3-pyridin-2-yl-quinoxalin-2-yl)-N,N-dimethyl-hexane-1,6-diamine

HRID 1266140Notes

Reaction equation

HRID 1266140 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]([Cl:19])=[C:7]([Cl:18])[CH:8]=2)[N:3]=1.[CH3:20][N:21]([CH3:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH2:28]>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][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][N:21]([CH3:29])[CH3:20])[C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)=[N:10]2

Participants

4

Reactant 2

HCID 2585446-(Dimethylamino)hexylamineHCID 185490312,6,7-Trichloro-3-pyridin-2-yl-quinoxaline

Product 1

HCID 18548996N'-(6,7-Dichloro-3-pyridin-2-yl-quinoxalin-2-yl)-N,N-dimethyl-hexane-1,6-diamineYield 60.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,6,7-trichloro-3-pyridin-2-yl-quinoxaline (0.50 g) and 6-dimethylamino-hexylamine (0.46 g) in toluene (25 mL) was refluxed under nitrogen atmosphere for 16 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 a yellow solid. Recrystallization from methanol and water gave the product as a fluffy yellow powder (0.41 g); mp 88-90° 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)
  6. customto give a yellow solid
  7. customRecrystallization from methanol and water

Sources & evidence

ORD record
ord-4c2d48b4f2ad470988f765872521791c
Source dataset
uspto-grants-2003_04
Patent number
US06548499B1

Reaction notes

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