Reaktion #5590

Reaktionsgleichung

acryloyl chloride

1-adamantaneamine

triethylamine

→

N-tricyclo[3.3.1.13,7 ]dec-1-yl-2-propenamide

Lösungsmittel

ethyl ether

ethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed on a rotary evaporator
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (100 ml)
3. 3
   Waschenwashed with 10 percent hydrochloric acid (100 ml) and water (50 ml)
4. 4
   Trocknendried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Sonstigethe solvent removed in vacuo
7. 7
   Sonstigeleaving an oily solid which
8. 8
   Sonstigewas crystallized from methanol-ethyl acetate-hexane

Vorschrift

A solution of acryloyl chloride (4.05 ml, 0.05 mole) in ethyl ether (25 ml) was added to a cold (+5° C.) solution of 1-adamantaneamine (7.65 g, 0.05 mole) and triethylamine (15.3 ml, 0.11 mole) in ethyl ether (300 ml) and the solution stirred for 72 hours at room temperature. The solvent was removed on a rotary evaporator. The residue was dissolved in ethyl acetate (100 ml), washed with 10 percent hydrochloric acid (100 ml) and water (50 ml), dried over sodium sulfate, filtered and the solvent removed in vacuo leaving an oily solid which was crystallized from methanol-ethyl acetate-hexane. The structure was confirmed by NMR.

Quelle