2-(Pyridin-3-yl)ethan-1-amine → 1-Ethyl-3,3,5-trimethyl-7-[3-(2-pyridin-3-ylethylamino) propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Participants

Reaction Conditions

Reaction Steps

1-Ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (5.3 mmol) was added to a methanol solution (100 ml) of 3-(2-aminoethyl)pyridine (3.3 g, 26.7 mmol), and stirred at 50° C. for 9 hours. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. Water was added to the residue, and extraction with dichloromethane was performed. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1→10:1). The purified product was concentrated under reduced pressure, and the residue was purified by basic silica gel column chromatography (ethyl acetate:methanol=1:0→10:1) again. The purified product was concentrated under reduced pressure to thereby obtain 1.57 g (yield: 70%) of 1-ethyl-3,3,5-trimethyl-7-[3-(2-pyridin-3-ylethylamino)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione as a yellow oil.

Provenance & Evidence