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

HRID 2787Notes

Reaction equation

HRID 2787 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]indole

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-a1beaa3b1b63410ca82b9562ddec3ef2
Source dataset
uspto-grants-1998_03
Patent number
US05731331

Reaction notes

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