1-Bromo-3-chloropropane → 2-(3-chloropropyl)-1H-1,2,3-benzotriazole
Reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.Br[CH2:11][CH2:12][CH2:13][Cl:14]>>[Cl:14][CH2:13][CH2:12][CH2:11][N:2]1[NH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:1]1Participants
Procedure
2-(3-Chloropropyl)-1H-1,2,3-benzotriazole (200 mg, 44%) was prepared from benzotriazole (300 mg, 2.52 mmol) and 1-bromo-3-chloro propane (397 mg, 2.77 mmol) according to the procedure of Example 291. The title compound was isolated as a yellow oil (26 mg, 54%) according to the method of Example 286, Step C 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 (44 mg, 0.24 mmol). 1H NMR (CDCl3) δ1.81-1.93 (m, 2H), 1.96-2.14 (m, 3H), 2.41 (td, 1H, J=3.7 , 11.7 Hz), 2.64-2.72 (m, 1H), 2.80-2.90 (m, 1H), 2.92-3.00 (m, 1H), 3.02-3.16 (m, 4H), 3.21-3.26 (m, 1H), 3.51-3.62 (m, 1H), 3.78-3.86 (m, 1H), 4.85 (t, 2H, J=7.0 Hz), 6.61 (t, 1H, J=7.5 Hz), 6.83 (d, 1H, J=6.6 Hz), 6.94 (dd, 1H, J=1.2, 8.1 Hz), 7.36-7.41 (m, 2H), 7.84-7.88 (m, 2H) ppm.
Sources & evidence
- ORD record
- ord-db51c8423e324f98879e1706993341f0
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06713471B1
Reaction notes
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