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 1266138Notes

Reaction equation

HRID 1266138 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 18549022N,N-Dimethyl-N'-(3-pyridin-2-yl-7,8-dihydro-6H-cyclopenta[g]quinoxalin-2yl)-cyclohexane-1,4-diamineYield 43.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9243754aa7994a89a3de227b87fa0525
Source dataset
uspto-grants-2003_04
Patent number
US06548499B1

Reaction notes

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