2,3,4,5-Tetrahydro-1H-benzo[d]azepine

1,2-Phenylacetonitrile was dissolved in 150 mL of DMF, and 15.86 g (142 mmol) of potassium tert-butoxide was added at an internal temperature of -10 to 0 °C. The mixture was stirred at 0–5 °C for 2 h. Then, 200 mL of water and 22 mL of 30% hydrochloric acid were added at 0–5 °C, and the mixture was stirred for 1 h. The mixture was filtered to obtain a crude product, which was then dissolved in 170 mL of methanol and recrystallized. After filtration and drying, 20.87 g of 2,3,4,5-TETRAHYDRO-1H-BENZO[D]AZEPINE was obtained, with a yield of 89%.

5-Azabenzocycloheptene is a reactant used in the synthesis of nonretinoid retinol binding protein 4 antagonists for potential treatment of atrophic age-related macular degeneration and Stargardt disease.