Potassium Carbonate → 5-Methoxy-3-{2-[4-(4-toluyl)piperdyl]ethyl}indole

HRID 867023Notes

Reaction equation

HRID 867023 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[NH:6][CH:5]=1.Cl.[C:16]1([CH3:28])[CH:21]=[CH:20][C:19]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:14][O:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][CH:5]=[C:4]2[CH2:3][CH2:2][N:25]1[CH2:26][CH2:27][CH:22]([C:19]2[CH:18]=[CH:17][C:16]([CH3:28])=[CH:21][CH:20]=2)[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 111078683-(2-bromoethyl)-5-methoxy-1H-indoleHCID 203515434-(4-Methylphenyl)piperidine hydrochloride

Product 1

HCID 203188855-Methoxy-3-{2-[4-(4-toluyl)piperdyl]ethyl}indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 8.8 g of 3-(2-bromoethyl)-5-methoxy indole in 100 ml of dimethylformamide is added to a stirring mixture of 4-(4-toluyl)piperidine hydrochloride [Example 5(a)] and 10.1 g of potassium carbonate in 400 ml of dimethylformamide and the reaction mixture is stirred at ambient temperature for 80 hours and then at 50° C. for 10 additional hours. It is cooled to ambient temperature, filtered, and 2 liters of water are added dropwise to produce a precipitate. The precipitate is triturated with ether and eluted with a 5% methanol in benzene solution through a silica gel column. The precipitate is recrystallized from an ethanol-water mixture to give off-white crystals, mp 131°-133° C., 5-methoxy-3-{2-[4-(4-toluyl)piperidyl]ethyl}indole.

Workup

  1. customat 50° C.
  2. temperatureIt is cooled to ambient temperature
  3. filtrationfiltered
  4. addition2 liters of water are added dropwise
  5. customto produce a precipitate
  6. customThe precipitate is triturated with ether
  7. washeluted with a 5% methanol in benzene solution through a silica gel column
  8. customThe precipitate is recrystallized from an ethanol-water mixture

Sources & evidence

ORD record
ord-f956e1b010bc4193ab4c4a9b26ebe8c7
Source dataset
uspto-grants-1978_07
Patent number
US04101663

Reaction notes

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