Reacción #446315

Ecuación de reacción

Water

Butyllithium

1,2,3,4-tetra -hydro-9-acridinamine

octyl chloroformate

→

octyl (1,2,3,4-tetrahydro-9-acridinyl)carbamate

Rendimiento 56.3%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat 0° C
2. 2
   Otrothe cooling bath removed
3. 3
   workup.STIRRINGthe solution stirred over the weekend
4. 4
   Extracciónthe mixture extracted with ethyl acetate
5. 5
   OtroThe ethyl acetate layer is separated
6. 6
   Otroevaporated
7. 7
   Otroto afford a yellow oil
8. 8
   LavadoChromatography (elution with isopropanol-chloroform (5:95))

Procedimiento

n Butyllithium, 0.033 mol, is added to a suspension of 6.5g (0.033 mol) of 1,2,3,4-tetra -hydro-9-acridinamine (Petrow, V., Journal of the Chemical Society, pages 634 to 637 (1947)) in 200 ml of tetrahydrofuran at 0° C. The mixture is stirred at 0° C. for 20 minutes, the cooling bath removed and 6.36 g (0.033 mol) of octyl chloroformate added and the solution stirred over the weekend. Water, 200 ml, is added and the mixture extracted with ethyl acetate. The ethyl acetate layer is separated and evaporated to afford a yellow oil. Chromatography (elution with isopropanol-chloroform (5:95)) affords 6.59 g of octyl (1,2,3,4-tetrahydro-9-acridinyl)carbamate, as a yelIow solid; mp 96-99° C.

Fuente