Potassium Carbonate → 1-[4-(4-Phenyl-1,2,3,6-tetrahydro-1-pyridyl)butyl]indole

HRID 1977252Notes

Reaction equation

HRID 1977252 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]1([C:7]2[CH2:12][CH2:11][N:10]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19]3)[CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 123407571-(4-Chlorobutyl)-1H-indole

Product 1

HCID 219978811-[4-(4-Phenyl-1,2,3,6-tetrahydro-1-pyridyl)butyl]indoleYield 57.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4.8 g (30 mmol) of 4-phenyl-1,2,3,6-tetrahydropyridine, 6.22 g of 1-(4-chlorobutyl)indole and 8.3 g of potassium carbonate in 100 ml of dimethylformamide is heated at 90° C. for 3 hours. Evaporation to dryness is then carried out at reduced pressure, the residue is redissolved in chloroform and washing is carried out repeatedly with water. The organic phase is dried with anhydrous sodium sulfate and evaporation is carried out at reduced pressure, a crude product being obtained which is purified by chromatography on silica gel. 5.7 g (17.3 mmol) of 1-[4-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)butyl]indole are obtained.

Workup

  1. customEvaporation to dryness
  2. dissolutionthe residue is redissolved in chloroform
  3. washwashing
  4. dry with materialThe organic phase is dried with anhydrous sodium sulfate and evaporation
  5. customa crude product being obtained which
  6. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b6861916c1d546a0a3e3f5bedbb2ce74
Source dataset
uspto-grants-2001_05
Patent number
US06232329B1

Reaction notes

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