Reacción #2045106

Ecuación de reacción

Indole

Formaldehyde

dimethylamine

indole

→

indole Mannich base

Rendimiento 57.0%

N-(Dimethylaminomethyl)-indole

Rendimiento 57.0%

Disolventes

Dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe suspension was stirred for 1 h in an ice/water bath
2. 2
   Otro24 h
3. 3
   Otroat RT
4. 4
   Otrothe organic layer was separated
5. 5
   OtroThe solvent was evaporated
6. 6
   Otrothe residue was chromatographed on a Chromatotron with dichloromethane/hexanes, 5:2 mixture as eluent
7. 7
   Otroto remove non-polar impurities
8. 8
   LavadoThis was followed by elution with dichloromethane/EtOAc, 5:1 to 1:1
9. 9
   OtroAppropriate fractions were collected

Procedimiento

Formaldehyde (37% in water, 0.19 mL, 2.6 mmol) was added to cooled (ice/water bath) aqueous dimethylamine (40% in water, 0.32 mL, 2.6 mmol). The mixture was stirred for 10 min and then indole 31 (0.3 g, 2.6 mmol) was added. The suspension was stirred for 1 h in an ice/water bath and then 24 h at RT. Indole was not completely dissolved. Dichloromethane (10 mL) was added and the organic layer was separated. The solvent was evaporated and the residue was chromatographed on a Chromatotron with dichloromethane/hexanes, 5:2 mixture as eluent to remove non-polar impurities. This was followed by elution with dichloromethane/EtOAc, 5:1 to 1:1. Appropriate fractions were collected to give indole Mannich base 32 as an oil (0.25 g, 57%) which was pure by TLC.

Fuente