3-BROMO-6,7,8,9-TETRAHYDRO-5H-IMIDAZO[1,2-A]AZEPINE synthesis

Yield:701298-97-7 81%

Reaction Conditions:

with N-Bromosuccinimide in tetrachloromethane; for 1 h;

Steps:

93.a

N-bromosuccinimide (1.3 g) was added to a solution of 6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepine (Hua, D. H. et al., J. Org. Chem., 59, 5084 (1994)) (1.0 g) in carbon tetrachloride (20 mL) and stirred for 1 hour. After an aqueous saturated sodium bicarbonate solution was added, the reaction solution was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and then concentrated. The resulting residue was purified with a silica gel column to obtain the title compound (1.29 g, 81%) as a pale yellow solid. NMR (300 MHz, CDCl3) δ: 1.66-1.90 (6H, m), 2.89-2.93 (2H,m), 3.98 (2H, t, J = 4.8), 6.80 (1H, s).

References:

EP1564213,2005,A1 Location in patent:Page/Page column 66-67