Dimethyl Sulfoxide → HCID 21703097, compound

HRID 1954250Notes

Reaction equation

HRID 1954250 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][CH2:11][CH2:12]Cl)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[F:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2CCCN.C([N:30]([CH2:33][CH3:34])CC)C.[OH2:35].[CH3:36]S(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[O:35][CH2:36][CH2:34][CH2:33][NH:30][CH2:12][CH2:11][O:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[CH2:1][CH2:2][CH2:3]2

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 8471TriethylamineHCID 39570663-(5-fluoro-1H-indol-3-yl)propan-1-amineHCID 12095943HCID 12095943, compound

Product 1

HCID 21703097HCID 21703097, compoundYield 43%

Conditions

Temperature
90 °C

Procedure

A solution of 2-(indan-5-yloxy)-ethylchloride (0.7 g, 3.5 mmol), 3-(5-fluoro-1H-indol-3-yl)-propylamine (1.01 g, 5.3 mmol) and triethylamine (0.53 g, 5 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 (5-10% methanol-methylene chloride) afforded 0.53 g (43%) 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

Sources & evidence

ORD record
ord-5dacf66a93f2447b941338db5011e6d1
Source dataset
uspto-grants-2000_09
Patent number
US06121307

Reaction notes

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