Reacción #1702075

Ecuación de reacción

sodium borohydride

2-bromo-5-methoxybenzaldehyde

cyclopropylamine

toluene

→

crude product

N-(2-bromo-5-methoxybenzyl)cyclopropanamine

Disolventes

water

methanol

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroIn a flask fitted with a Dean-Stark trap
2. 2
   Temperaturaat reflux for 4 hours
3. 3
   ConcentraciónThe solution was then concentrated
4. 4
   Otroto give a yellow oil to which
5. 5
   TemperaturaThe reaction mixture was cooled on icebath
6. 6
   workup.ADDITIONAfter complete addition
7. 7
   workup.STIRRINGthe reaction mixture was stirred 2 hours at room temperature

Procedimiento

In a flask fitted with a Dean-Stark trap was introduced 2-bromo-5-methoxybenzaldehyde (5.68 g, 26.41 mmol), cyclopropylamine (3.02 g, 52.83 mmol) and toluene (70 ml). The reaction mixture was stirred at room temperature for 1 hour and then at reflux for 4 hours. The solution was then concentrated to give a yellow oil to which was added methanol (30 ml). The reaction mixture was cooled on icebath followed by portionwise addition of sodium borohydride (2.00 g, 52.83 mmol). After complete addition, the reaction mixture was stirred 2 hours at room temperature, and then water (70 ml) was added. The crude product was isolated by extraction with dichloromethane and the combined organic phases were dried over sodium sulfate, filtered, and finally evaporated under reduced pressure.

Fuente