Ethanolamine → HCID 22556872, compound

HRID 910065Notes

Reaction equation

HRID 910065 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].CS(O[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][CH:18]=[CH:17]2)(=O)=O>C(O)C.C(OCC)(=O)C>[OH:2][CH2:1][CH2:3][NH:4][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][CH:18]=[CH:17]2

Participants

5

Reactant 2

HCID 700EthanolamineHCID 22556790HCID 22556790, compound

Product 1

HCID 22556872HCID 22556872, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add ethanolamine (5 mL, 82 mmol) to a solution of 7-(2-(methanesulfonyloxy)eth-1-yl)indole (0.79 g, 3.3 mmol) in ethanol (50 mL) and stir the reaction mixture at reflux overnight Dilute with ethyl acetate (150 mL), wash sequentially with water (3×50 mL) and saturated aqueous sodium chloride (2×50 mL), dry over sodium sulfate, filter, and concentrate under reduced pressure to provide 7-(2-(N-[2-hydroxyeth-1-yl]amino)eth-1-yl)indole as a light-brown solid (0.57 g, 85%).

Workup

  1. temperatureat reflux overnight
  2. washwash sequentially with water (3×50 mL) and saturated aqueous sodium chloride (2×50 mL)
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-95452bd2c7cc4ffebba78abb6447426b
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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