Reacción #1178422

Ecuación de reacción

(3,5-dichloro-phenyl)-(1-nitro-cyclohexyl)-methanol

→

(1-amino-cyclohexyl)-(3,5-dichloro-phenyl)-methanol

Rendimiento 82.4%

Disolventes

methanol

HCl

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónfiltered through Celite
2. 2
   LavadoThe filter cake was washed with methanol (2×100 mL)
3. 3
   Otrothe filtrate was evaporated to dryness
4. 4
   workup.ADDITIONThe residue was treated with 5% aqueous NaOH (100 mL)
5. 5
   Extracciónextracted with ethyl acetate (2×200 mL)
6. 6
   SecadoThe combined organic extracts were dried over Na2SO4
7. 7
   Otroevaporated

Procedimiento

To a stirred solution of (3,5-dichloro-phenyl)-(1-nitro-cyclohexyl)-methanol (5.87 g, 19.3 mmol) in methanol (40 mL) and concentrated HCl (10 mL), cooled to ˜5° C., was added zinc powder. The mixture was stirred at room temperature overnight and filtered through Celite. The filter cake was washed with methanol (2×100 mL) and the filtrate was evaporated to dryness. The residue was treated with 5% aqueous NaOH (100 mL) and extracted with ethyl acetate (2×200 mL). The combined organic extracts were dried over Na2SO4 and evaporated to leave (1-amino-cyclohexyl)-(3,5-dichloro-phenyl)-methanol (4.36 g) as a white solid. 1H NMR (500 MHz, CDCl3) δ (ppm): 7.25 (s, 1H), 7.185 (s, 2H), 4.21 (s, 1H), 1.55 (m, 4H), 1.3 (m, 3H), 1.1 (m, 3H).

Fuente