Morpholine → 3,4-Dihydro-1,4-dimethyl-2[2-(4-morpholinyl)ethyl]-1H-[1,3,5]triazepino[3,2-a]benzimidazol-5(2H)-one
Reaction equation
Cl[CH2:2][CH2:3][CH:4]1[N:17]([CH3:18])[C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[C:7](=[O:19])[N:6]([CH3:20])[CH2:5]1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>>[CH3:18][N:17]1[C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[C:7](=[O:19])[N:6]([CH3:20])[CH2:5][CH:4]1[CH2:3][CH2:2][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1Participants
3
Conditions
- Temperature
- 60 °C
Procedure
To 3.0 g (0.0103 mol) of 2-(2-chloroethyl)-3,4-dihydro-1,4-dimethyl-1H-[1,3,5]triazepino[3,2-a]benzimidazol-5(2H)-one was added 20 mL of morpholine. The mixture was stirred at 60° C. for 4 hr. The morpholine was removed at 60° C. and approximately 1 mm Hg. The residue was partitioned between 100 mL of CH2Cl2 and 100 mL of 1N NaOH. The basic layer was reextracted with 50 mL of CH2Cl2. The combined organic extracts were dried over Na2SO4, filtered, and concentrated by rotary evaporation. The residue was crystallized from isopropyl alcohol to afford 2.1 g (59%) of white analytically pure crystals, mp 149°-151.5° C.