Reaction #433629

Reaction equation

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

Solvents

hexane

methylene chloride

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   Temperaturereflux 48 h
2. 2
   Extractionextracted by ethyl acetate (3×20 ml)
3. 3
   Washwashed to times by water and two times by brine
4. 4
   ExtractionThe combined extract
5. 5
   Dryingdried by the mixture of sodium sulfate and potassium carbonate
6. 6
   OtherAfter removing of solvents the rest
7. 7
   Otherwas purified by chromatography (silica gel, methanol ethyl acetate 1:1)

Procedure

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).

Source