Toluene → 3-(4-Methoxy-phenoxy)-propylamine

Under an argon atmosphere, 3-(4-methoxyphenoxy)propionitrile (5.0 g) was dissolved in tetrahydrofuran (20 mL), and borane-tetrahydrofuran complex (1.02 mol/L, 30.0 mL) was added dropwise at 80° C. for 10 minutes. After stirring for 3 hours at the same temperature, the reaction liquor was returned to room temperature. In an ice-cold bath, a 4 N aqueous sodium hydroxide solution (30 mL) was added for 10 minutes. After 10 minutes, the mixture was stirred at room temperature for 5 minutes, and then stirred at 80° C. for 12 hours. The mixture was returned to room temperature, and toluene (100 mL) was added, and the mixture was stirred for 1 hour, and then insoluble material was removed using Celite. An organic layer was isolated, and washed with water (100 mL×2 times) and saturated brine (100 mL), and then dried over anhydrous sodium sulfate (80 g). The resultant was filtered, and then the filtrate was concentrated under reduced pressure to obtain a white solid (4.0 g, 79.0%).

1. additionborane-tetrahydrofuran complex (1.02 mol/L, 30.0 mL) was added dropwise at 80° C. for 10 minutes
2. customwas returned to room temperature
3. waitAfter 10 minutes
4. stirringthe mixture was stirred at room temperature for 5 minutes
5. stirringstirred at 80° C. for 12 hours
6. customwas returned to room temperature
7. stirringthe mixture was stirred for 1 hour
8. custominsoluble material was removed
9. customAn organic layer was isolated
10. washwashed with water (100 mL×2 times) and saturated brine (100 mL)
11. dry with materialdried over anhydrous sodium sulfate (80 g)
12. filtrationThe resultant was filtered
13. concentrationthe filtrate was concentrated under reduced pressure

ORD-Eintrag

ord-43c4d507f2fd4ad0a4f218cedf516143

Quelldatensatz

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07790903B2