[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][NH:8][CH2:7][C:6]=2[CH:12]=1.CCN(CC)CC.[C:20](OC(=O)C)(=[O:22])[CH3:21]>C1COCC1>[C:20]([CH:9]1[NH:8][CH2:7][C:6]2[CH:12]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[NH:11][CH2:10]1)(=[O:22])[CH3:21]7-chloro-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine (12.5 mmol) was dissolved in a mixture of THF (100 mL), Et3N (19.1 mmol) and acetic anhydride (12.4 mmol). The reaction mixture was heated under reflux for 18 h, cooled to room temperature and partitioned between H2O and EtOAc. The aqueous phase was extracted again 2× with EtOAc and the combined organic layers were dried over MgSO4, filtered and concentrated to a yellow, oily solid. The crude material was purified by column chromatography on silia eluting with EtOAc to yield 3-acetyl-7-chloro-1,2,3,5-tetrahydro-4H-[1,4]benzodiazepine (2.8 mmol, 22%) as a clear oil.
Wird geladen…
