1-Bromo-3-chloropropane → 2-(3-chloropropyl)-1H-1,2,3-benzotriazole

Participants

Reaction Steps

Benzotriazole (303 mg, 2.54 mmol) and 1-bromo-3-chloro propane (437 mg, 2.77 mmol) were used according to the method of Example 291, Step A to yield 2-(3-chloropropyl)-1H-1,2,3-benzotriazole (182 mg, 37%). The title compound was prepared according to Example 286, Step C as a yellow oil (20 mg, 40%) from (8aS,12aR)-6,7,8a,9,10,11,12,12a-octahydro-5H-pyrido[4,3-b][1,4]thiazepino[2,3,4-hi]indole (30 mg, 0.12 mmol) and 2-(3-chloropropyl)-1H-1,2,3-benzotriazole (48 mg, 0.24 mmol). 1H NMR (CDCl3) δ1.84-1.94 (m, 3H), 1.99-2.20 (m, 2H), 2.25-2.52 (m, 5H), 2.64-2.72 (m, 1H), 2.74-2.82 (m, 1H), 2.88-3.00 (m, 1H), 3.02-3.18 (m, 2H), 3.22-3.28 (m, 1H), 3.51-3.61 (m, 1H), 3.74-3.85 (m, 1H), 4.80 (t, 2H, J=6.7 Hz), 6.61 (t, 1H, J=7.5 Hz), 6.92 (dd, 2H, J=6.6, 24.9 Hz), 7.35-7.41 (m, 2H), 7.83-7.85 (m, 2H) ppm.

Provenance & Evidence