3-Azido-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one → 3-Amino-2,3,4,5-tetrahydro-1H-benzazepin-2-one

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Reaction Steps

To a suspension of 10.0 g (49.4 mmol) of 3-azido-2,3,4,5-tetrahydro-1H-[1]-benzazapin-2-one (Example 3 above) in 100 mL of methanol/ethanol (1:1) was added 1 g of 10% palladium on charcoal and the flask was purged with nitrogen and charged with 55 psig hydrogen. The mixture was shaken for 5 h, filtered through celite and concentrated. The residue was recrystallized from MEOH to give 6.77 g (78%) in two crops. 1H NMR (300 MHz, CDCl3) d 8.38 (1H, bs), 7.3-7.1 (3H, m), 6.98 (1H, d, J=8 Hz), 3.42 (1H, dd, J=11, 7 Hz), 2.90 (1H, m), 2.70-2.40 (2H, m), 1.89 (1H, m), 1.78 (bs, 2H).

Provenance & Evidence