N,N-Dimethyl-1,4-cyclohexanediamine → N,N-Dimethyl-N'-(3-pyridin-2-yl-7,8-dihydro-6H-cyclopenta[g]quinoxalin-2yl)-cyclohexane-1,4-diamine

HRID 1266138

Reaktionsgleichung

Reaktionsgleichung von HRID 1266138
Cl[C:2]1[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[N:4][C:5]2[CH:6]=[C:7]3[CH2:14][CH2:13][CH2:12][C:8]3=[CH:9][C:10]=2[N:11]=1.[CH3:21][N:22]([CH3:30])[CH:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1>C1(C)C=CC=CC=1>[CH3:21][N:22]([CH3:30])[CH:23]1[CH2:28][CH2:27][CH:26]([NH:29][C:2]2[C:3]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:4][C:5]3[CH:6]=[C:7]4[CH2:14][CH2:13][CH2:12][C:8]4=[CH:9][C:10]=3[N:11]=2)[CH2:25][CH2:24]1

Komponenten

4

Edukt 2

HCID 345823N,N-Dimethyl-1,4-cyclohexanediamineHCID 185489952-chloro-3-pyridin-2-yl-7,8-dihydro-6H-cyclopenta[g]quinoxaline

Produkt 1

HCID 18549022N,N-Dimethyl-N'-(3-pyridin-2-yl-7,8-dihydro-6H-cyclopenta[g]quinoxalin-2yl)-cyclohexane-1,4-diamineAusbeute 43,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 2-chloro-3-pyridin-2-yl-7,8-dihydro-6H-cyclopenta[g]quinoxaline (0.5 g) and N,N-dimethyl-cyclohexane-1,4-diamine (0.51 g) in toluene (30 mL) was refluxed under nitrogen atmosphere for 16 hours. The reaction was cooled, filtered, and concentrated under vacuum. The residue was purified by flash chromatography (silica gel, 1:19 methanol/dichloromethane) to give a yellow solid. Recrystallization from methanol and water gave the product as yellow crystals ( 0.3 g); mp 158-161° C.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by flash chromatography (silica gel, 1:19 methanol/dichloromethane)
  5. customto give a yellow solid
  6. customRecrystallization from methanol and water

Quellen und Nachweise

ORD-Eintrag
ord-9243754aa7994a89a3de227b87fa0525
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06548499B1

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