Reacción #458365

Ecuación de reacción

N-t-butyl-N-cyclohexylcyanamide

lithium diisopropylamide

octahydroacridine

→

title compound

4-Cyano-1,2,3,4,5,6,7,8-octahydroacridine

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched with water
2. 2
   Extracciónextracted with toluene
3. 3
   Lavadothe organic phase washed with water
4. 4
   Otrodried
5. 5
   Otroevaporated
6. 6
   workup.DISSOLUTIONThe residue, dissolved in ethyl acetate

Procedimiento

A solution of lithium diisopropylamide [ex 1.55M BuLi/hexane (32.3 ml, 50 mM), diisopropylamine (3.5 ml, 25 mM), tetrahydrofuran (20 ml)] maintained at 0° C. under an argon atmosphere was treated with a solution of octahydroacridine (4.68 g, 25 mM) in the tetrahydrofuran (10 ml). After 0.5 hours a solution of N-t-butyl-N-cyclohexylcyanamide (4.6 g, 28 mM) in tetrahydrofuran (10 ml) was added and the mixture stirred overnight. The reaction was quenched with water, extracted with toluene and the organic phase washed with water, dried and evaporated. The residue, dissolved in ethyl acetate, was passed through a short silica column to yield the title compound. (3.8 g) mp. 88°-90° C.

Fuente