Reacción #88208

Ecuación de reacción

NaBH4

p-Anisaldehyde

4-methoxybenzylamine

toluene

→

desired product

bis-(4-methoxy-benzyl)-amine

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrofitted with a condenser
2. 2
   Otrowas removed from the reaction mixture
3. 3
   TemperaturaThe reaction was cooled
4. 4
   Concentraciónconcentrated
5. 5
   workup.DISSOLUTIONThe residue was dissolved in MeOH (120 mL)
6. 6
   TemperaturaThe reaction was slowly heated to reflux
7. 7
   TemperaturaAfter 2 h at reflux
8. 8
   Temperaturathe reaction was cooled to room temperature
9. 9
   Concentraciónconcentrated
10. 10
    workup.DISSOLUTIONThe residue was dissolved in EtOAc
11. 11
    LavadoThe organic layer was washed (3×H2O and brine)
12. 12
    Secadodried (Na2SO4)
13. 13
    Concentraciónconcentrated

Procedimiento

p-Anisaldehyde (411 mmol), 4-methoxybenzylamine (411 mmol) and toluene (500 mL) were combined in a round bottomed flask fitted with a condenser and a Dean-Stark trap. The reaction was refluxed for 1 h during which water was removed from the reaction mixture. The reaction was cooled and concentrated. The residue was dissolved in MeOH (120 mL). The mixture was cooled to 5° C. and NaBH4 (205 mmol) was added in portions over 45 min. The reaction was slowly heated to reflux. After 2 h at reflux, the reaction was cooled to room temperature and concentrated. The residue was dissolved in EtOAc. The organic layer was washed (3×H2O and brine), dried (Na2SO4) and concentrated to yield the desired product.

Fuente