Triethylamine → HCID 9870825, compound

HRID 1266144Notes

Reaction equation

HRID 1266144 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.Cl.Cl.[C:22]1([CH:28]([NH2:38])[CH2:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>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:38][CH:28]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:29][CH2:30][CH2:31][N:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1)[C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)=[N:10]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 185490312,6,7-Trichloro-3-pyridin-2-yl-quinoxalineHCID 70034347HCID 70034347, compound

Product 1

HCID 9870825HCID 9870825, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution 2,6,7-trichloro-3-pyridin-2-yl-quinoxaline (0.31 g) and alpha-phenyl-1-piperdine-butylamine dihydrochloride (0.31 g) in toluene (25 mL) was added triethylamine (0.50 mL). The resulting mixture was refluxed under nitrogen atmosphere for 36 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 (0.32 g); mp 125-127° C.

Workup

  1. temperatureThe resulting mixture was refluxed under nitrogen atmosphere for 36 hours
  2. temperatureAfter refluxing
  3. temperaturethe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography (silica gel, 1:9 methanol/dichloromethane)
  7. customto give a yellow solid
  8. customRecrystallization from methanol and water

Sources & evidence

ORD record
ord-8c44b69b87524de4b529efb991c8dc2c
Source dataset
uspto-grants-2003_04
Patent number
US06548499B1

Reaction notes

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