Water → HCID 9844921, compound

HRID 1954251Notes

Reaction equation

HRID 1954251 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:7]Cl.[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[CH2:29][CH2:30]N.[CH2:32]([N:34](CC)CC)C.O>CS(C)=O>[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[CH2:29][CH2:30][CH2:32][NH:34][CH2:7][CH:6]([O:5][C:4]1[CH:15]=[CH:16][CH:17]=[CH:18][C:3]=1[O:2][CH3:1])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1646825-FluorotryptamineHCID 21703090HCID 21703090, compound

Product 1

HCID 9844921HCID 9844921, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-(2-methoxy-phenoxy)-2-phenyl-ethylchloride (0.71 g, 2.7 mmol), 2-(5-fluoro-1H-indol-3-yl)-ethylamine (1.04 g, 5.4 mmol) and triethylamine (0.75 ml, 5.4 mmol) in anhydrous dimethylsulfoxide (20 ml) was allowed to stir for 12 hours at 90° C. The mixture was poured into water (100 ml) and extracted with methylene chloride (3×100 ml). The organic layer was washed with water (3×100 ml), dried over anhydrous sodium sulfate, filtered, and the solvent was removed under vacuum. Chromatography (7% methanol-methylene chloride plus ammonium hydroxide) afforded 0.15 g (13%)of parouduct of product as a yellow oil.

Workup

  1. extractionextracted with methylene chloride (3×100 ml)
  2. washThe organic layer was washed with water (3×100 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under vacuum
  6. customChromatography (7% methanol-methylene chloride plus ammonium hydroxide) afforded 0.15 g (13%)of parouduct of product as a yellow oil

Sources & evidence

ORD record
ord-75e64a548481457cb595e5314d5a2a58
Source dataset
uspto-grants-2000_09
Patent number
US06121307

Reaction notes

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