1,3,4,5-Tetrahydro-2H-1-benzazepin-2-one → 2,3,4,5-tetrahydro-1H-1-benzazepine

Temperature

0 °C

To a solution of 1,3,4,5-tetrahydrobenzo[b]azepin-2-one (12.9 g, 80.0 mmol) in 720 mL of tetrahydrofuran was added 80 mL of lithium aluminum hydride (1 M solution in tetrahydrofuran). The reaction mixture was stirred at reflux for 3 hours and cooled to 0° C. The reaction was quenched by the sequential addition of 3 mL of water, 3 mL of 15% sodium hydroxide, and 9 mL of water. The mixture was filtered through Celite and the filter cake rinsed with ethyl acetate. The filtrate was concentrated under reduced pressure to provide 10.0 g (85%) of the desired compound as an orange solid.

1. temperatureat reflux for 3 hours
2. customThe reaction was quenched by the sequential addition of 3 mL of water, 3 mL of 15% sodium hydroxide, and 9 mL of water
3. filtrationThe mixture was filtered through Celite
4. washthe filter cake rinsed with ethyl acetate
5. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-4064ede10cac43df8ca4a0121de7a409

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06743785B2