3-Pyridinecarboxaldehyde → 1-(3-Pyridyl)methyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Beteiligte Stoffe

Reaktionsschritte

To solution of 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine from Example 15A (0.50 g, 3.38 mmol) in 1% acetic acid/methanol (25 ml), at room temperature, was added pyridine-3-carboxaldehyde (0.35 ml, 03.72 mmol). The mixture was stirred at reflux for 18 h and then allowed to cool to room temperature. Sodium borohydride (0.050 g, 0.80 mmol) was added. The mixture was stirred for 2 h and then evaporated in vacuo. The residue was partitioned between EtOAc and saturated sodium bicarbonate solution. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacua. The residue was purified by flash chromatography on silica (eluant EtOAc) to give a white solid; yield 0.386 g (40%).

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