Nitrogen → 2,3,4,5-tetrahydro-1H-1-benzazepine

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Reaction Steps

Under anhydrous conditions and N2 atmosphere, 1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (100 mg) in THF (5 ml) was treated with LiAlH4 (0.65 ml @ 1.0M in THF). The resulting solution was heated at reflux for 1 hr. The reaction was quenched by addition to a small amount of ice. The resulting mixture was diluted with a large excess of CH3CN (˜50:1) and filtered. The filtrate was concentrated in vacuo to give 84 mg of the titled product. 1H NMR (300 MHz, CDCl3) 1.69 (m, 2H), 1.86 (m, 2H), 2.82 (m, 2H), 3.10 (m, 2H), 3.6 (bs, 1H), 6.80 (d, J=7.8 Hz, 1H), 6.88 (t, J=7.3 Hz, 1H), 7.09 (dt, J=7.6 Hz, J=1.4 Hz, 1H), 7.15 (d, J=7.4 Hz, 1H).

Provenance & Evidence