Sodium Iodide → (3RS)-2,3-dihydro-1-(isoquinolin-1-yl)methyl-5-phenyl-3-phthalimido-1H-1,4-benzodiazepin-2-one

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Reaction Steps

To a suspension of sodium hydride (0.11 g in a 64% dispersion of mineral oil) in dry N,N-dimethylformamide (20 ml) was added slowly (3RS)-2,3-dihydro-5-phenyl-3-phthalimido-1H-1,4-benzodiazepin-2-one (1.00 g) at ambient temperature, and stirred for 2 hours. To the mixture was added sodium iodide (0.413 g) and followed dropwise a solution of 1-chloromethylisoquinoline (0.695 g) in dry N.N-dimethylformamide (5 ml) at ambient temperature and stirred overnight. The mixture was concentrated in vacuo and the residue was taken up with ethyl acetate. The organic layer was washed with saturated sodium carbonate aqueous solution, and dried over sodium sulfate, filtered and concentrated in vacuo to give a crude product. The crude product was purified by column chromatography with chloroform as an eluent to give (3RS)-2,3-dihydro-1-(isoquinolin-1-yl)methyl-5-phenyl-3-phthalimido-1H-1,4-benzodiazepin-2-one (0.54 g) as a colorless form.

Provenance & Evidence