(3-Aminopropyl)diethanolamine → HCID 9954684, compound

HRID 1266143Notes

Reaction equation

HRID 1266143 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.[OH:20][CH2:21][CH2:22][N:23]([CH2:28][CH2:29][OH:30])[CH2:24][CH2:25][CH2:26][NH2:27]>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:27][CH2:26][CH2:25][CH2:24][N:23]([CH2:28][CH2:29][OH:30])[CH2:22][CH2:21][OH: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 21088(3-Aminopropyl)diethanolamineHCID 185490312,6,7-Trichloro-3-pyridin-2-yl-quinoxaline

Product 1

HCID 9954684HCID 9954684, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,6,7-trichloro-3-pyridin-2-yl-quinoxaline (0.50 g) and 3-[bis(2-hydroxy-ethyl)amino]-propylamine (0.51 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 yellow plate like crystals (0.55 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-bf36f5cd81b34443941774d3ad7fb5ca
Source dataset
uspto-grants-2003_04
Patent number
US06548499B1

Reaction notes

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