反应详情

温度

80 °C

A neat mixture of 2-tetralone (0.552 g, 3.78 mmol), 1-(3-aminopropyl)-4-methylpiperazine (0.713 g, 4.54 mmol, 1.2 eq), and titanium (IV) isopropoxide (1.44 g, 5.67 mmol, 1.5 eq) was heated at 80° C. for 3 hours. The mixture was cooled to 0° C., diluted with 5 mL of MeOH, and then treated with NaBH4 (0.143 g, 3.78 mmol, 1 eq, adding portionwise). The resulting mixture was stirred at 0° C. for 30 min and then at room temperature for 12 hours. The reaction mixture was concentrated in vacuo, treated with water (3 mL) and then MeOH (30 mL), filtered through Celite. The filtrate was concentrated in vacuo, and the residue was redissolved in water (25 mL) and extracted with CHCl3 (3×25 mL). The combined CHCl3 extracts were dried (MgSO4) and concentrated to give [3-(4-methyl-piperazin-1-yl)-propyl]-(1,2,3,4-tetrahydro-naphthalen-2-yl)-amine as a dark brown oil (0.721 g, 67%). The crude intermediate was used in the subsequent step without further purification.

1. temperatureThe mixture was cooled to 0° C.
2. additionadding portionwise)
3. waitat room temperature for 12 hours
4. concentrationThe reaction mixture was concentrated in vacuo
5. additiontreated with water (3 mL)
6. filtrationMeOH (30 mL), filtered through Celite
7. concentrationThe filtrate was concentrated in vacuo
8. dissolutionthe residue was redissolved in water (25 mL)
9. extractionextracted with CHCl3 (3×25 mL)
10. dry with materialThe combined CHCl3 extracts were dried (MgSO4)
11. concentrationconcentrated