Reaktion #433629

Reaktionsgleichung

diethyl aluminum chloride

1-adamantanecarbonyl chloride

(N-Methyl-2-piperidinyl)methyl-1H-indole

sodium hydroxide

→

1-(N-Methyl-2-piperidinyl)methyl-3-(1-adamantanecarbonyl)-1H-indole

Lösungsmittel

hexane

methylene chloride

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturreflux 48 h
2. 2
   Extraktionextracted by ethyl acetate (3×20 ml)
3. 3
   Waschenwashed to times by water and two times by brine
4. 4
   ExtraktionThe combined extract
5. 5
   Trocknendried by the mixture of sodium sulfate and potassium carbonate
6. 6
   SonstigeAfter removing of solvents the rest
7. 7
   Sonstigewas purified by chromatography (silica gel, methanol ethyl acetate 1:1)

Vorschrift

To the stirring solution of the diethyl aluminum chloride (1.5 ml 1 M soln. in hexane, 180.8 mg, 1.5 mmol) in 10 ml absolute methylene chloride was added at room temp. 298.0 mg (1.5 mmol) 1-adamantanecarbonyl chloride in 5 ml of methylene chloride and the reaction mixture was stirred 15 min. The solution of (N-Methyl-2-piperidinyl)methyl-1H-indole (228.3 mg, 1.0 mmol) in 5 ml of methylene chloride was added during 3 min and mixture was stirred and reflux 48 h. The reaction was work-up by addition of 20 ml 2M solution of sodium hydroxide and extracted by ethyl acetate (3×20 ml), washed to times by water and two times by brine. The combined extract dried by the mixture of sodium sulfate and potassium carbonate. After removing of solvents the rest was purified by chromatography (silica gel, methanol ethyl acetate 1:1).

Quelle