Water → HCID 9819228, compound

HRID 1954242Notes

Reaction equation

HRID 1954242 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][CH2:13][NH2:14])[C:5]=2[O:4][CH2:3][CH2:2]1.Br[CH2:16][CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1.C(N(CC)CC)C.O>CS(C)=O>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][CH2:13][NH:14][CH2:16][CH2:17][C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][CH:19]=3)[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 769243-(2-Bromoethyl)indoleHCID 11275594HCID 11275594, compound

Product 1

HCID 9819228HCID 9819228, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-(2,3-dihydrobenzo[1,4]dioxin-5-yloxy) ethylamine (0.38 g, 1.9 mmol), 3-(2-bromoethyl)-indole (0.24 g, 1.1 mmol) and triethylamine (0.22 g, 2.2 mmol) in anhydrous dimethylsulfoxide (20 ml) was allowed to stir for 14 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 (3×150 ml), dried over anhydrous sodium sulfate, filtered and the solvent was removed under vacuum. Chromatography (10% methanol-methylene chloride plus ammonium hydroxide) afforded 0.19 g (52%) as a yellow oil.

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
  6. customChromatography (10% methanol-methylene chloride plus ammonium hydroxide) afforded 0.19 g (52%) as a yellow oil

Sources & evidence

ORD record
ord-ce16f05d0e1945e2894fe51e996ca597
Source dataset
uspto-grants-2000_09
Patent number
US06121307

Reaction notes

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