反应详情

温度

70 °C

To a solution of 1,2,3,4-tetrahydroquinoline (505 mg, 3.79 mmol) and 1-bromo-3-chloro propane (1.77 g, 11 mmol) in 1,4-dioxane (6 mL) was added Et3N (1.90 g, 19 mmol). The reaction mixture was stirred at 70° C. for 17 h, and quenched by addition of H2O (2 mL). Reaction was diluted with Et2O (100 mL) and washed with brine (100 mL), dried over MgSO4 and concentrated in vacuo. Purification by column chromatography (hexanes:EtOAc 49:1) yielded 1-(3-chloropropyl)-1,2,3,4-tetrahydroquinoline (187 mg, 24%) as a colorless oil. The title compound was isolated as a yellow oil (22 mg, 43%) 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 1-(3-chloropropyl)-1,2,3,4-tetrahydroquinoline (51 mg, 0.24 mmol). 1H NMR (CDCl3) δ1.77-2.19 (m, 10H), 2.24-2.41 (m, 2H), 2.61-2.69 (m, 1H), 2.75-2.84 (m, 3H), 2.91-3.02 (m, 1H), 3.10-3.21 (m, 2H), 3.26-3.34 (m, 5H), 3.52-3.61 (m, 1H), 3.77-3.96 (m, 1H), 6.49-6.65 (m, 3H), 6.85 (d, 1H, J=7.3 Hz), 6.92-6.96 (m, 2H), 6.99-7.05 (m, 1H) ppm.

1. customquenched by addition of H2O (2 mL)
2. customReaction
3. washwashed with brine (100 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated in vacuo
6. customPurification by column chromatography (hexanes:EtOAc 49:1)