Reaction #433628

Reaction equation

3-quinolinecarbonyl chloride

AlCl3

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

sodium hydroxide

→

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

Solvents

methylene chloride

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture stirred 36 h
2. 2
   Extractionextracted by ethyl acetate (3×20 ml)
3. 3
   ExtractionThe combined extract
4. 4
   Dryingdried by sodium sulfate
5. 5
   OtherAfter removing of solvents the rest (0.365 g)
6. 6
   Otherwas purified by chromatography (silica gel, toluene-triethylamine, 10:1)

Procedure

To the suspension of 200 mg (1.5 mmol) of anhydrous AlCl3 in 8 ml absolute methylene chloride was added 287.4 mg (1.5 mmol) 3-quinolinecarbonyl chloride in 5 ml methylene chloride and the reaction mixture was stirred 30 min at room 22–25° C. The (N-Methyl-2-piperidinyl)methyl-1H-indole 228.3 mg (1.0 mmol) in 5 ml of methylene chloride was added by dropwise during 1.5 h and the mixture stirred 36 h. The reaction was work-up by addition of 20 ml 2M solution of sodium hydroxide and extracted by ethyl acetate (3×20 ml). The combined extract dried by sodium sulfate. After removing of solvents the rest (0.365 g) was purified by chromatography (silica gel, toluene-triethylamine, 10:1).

Source