Water → [3-(5-Fluoro-1H-indol-3-yl)propyl]-[2-(1H-indol-4-yloxy)-ethyl]-amine

HRID 1596784Notes

Reaction equation

HRID 1596784 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([O:10][CH2:11][CH2:12]Cl)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[F:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](NCCC)=[CH:18]2.O>CS(C)=O>[F:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH2:4][CH2:3][CH2:2][NH:1][CH2:12][CH2:11][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[CH:2][NH:1]2

Participants

5

Reactant 3

HCID 962WaterHCID 106317214-(2-chloroethoxy)-1H-indoleHCID 699484305-Fluoro-indolyl-3-propylamine

Product 1

HCID 11428089[3-(5-Fluoro-1H-indol-3-yl)propyl]-[2-(1H-indol-4-yloxy)-ethyl]-amineYield 85.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-(1H-indol4-yloxy)ethylchloride (0.7 g, 3.6 mmol), 5-fluoro-indolyl-3-propylamine (1.0 g, 5.4 mmol) in dimethylsulfoxide (20 ml) was allowed to stir for 12 hours at 90° C. The reaction mixture was poured into water (100 ml) and extracted with methylene chloride (3×100 ml). The organic layer was washed with water (3×150 ml), dried over anhydrous sodium sulfate, filtered and the solvent was removed under vacuum. Chromatography (5%-10% methanol-methylene chloride) afforded 0.54 g (43%) of product as a white solid: mp 70-73° C.

Workup

  1. extractionextracted with methylene chloride (3×100 ml)
  2. washThe organic layer was washed with water (3×150 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-e661e7585a29453f8de045726ea79d09
Source dataset
uspto-grants-2001_09
Patent number
US06291683B1

Reaction notes

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