Reaktion #458365

Reaktionsgleichung

N-t-butyl-N-cyclohexylcyanamide

lithium diisopropylamide

octahydroacridine

→

title compound

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

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with water
2. 2
   Extraktionextracted with toluene
3. 3
   Waschenthe organic phase washed with water
4. 4
   Sonstigedried
5. 5
   Sonstigeevaporated
6. 6
   workup.DISSOLUTIONThe residue, dissolved in ethyl acetate

Vorschrift

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.

Quelle