Ethanolamine → HCID 22556872, compound

HRID 983939Notes

Reaction equation

HRID 983939 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][CH:14]=[CH:13]2)(=O)=O.[CH2:17]([CH2:19][NH2:20])[OH:18]>C(O)C.C(OCC)(=O)C>[OH:18][CH2:17][CH2:19][NH:20][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][CH:14]=[CH:13]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

To a solution of 7-(2-(methanesulfonyloxy)eth-1-yl)indole (0.79 g, 3.3 mmol) in ethanol (50 mL) was added ethanolamine (5 mL, 82 mmol) and the reaction stirred at reflux overnight. The reaction was diluted with ethyl acetate (150 mL) and washed with water (3×50 mL), saturated aqueous sodium chloride (2×50 mL) and dried over sodium sulfate, filtered and concentrated under reduced pressure to provide 0.57 g (85%) 7-(2-(N-[2-hydroxyeth-1-yl]amino)eth-1-yl)indole as a light-brown solid.

Workup

  1. temperatureat reflux overnight
  2. washwashed with water (3×50 mL), saturated aqueous sodium chloride (2×50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55117a2668ba49fd9dd8420e531136b0
Source dataset
uspto-grants-2005_03
Patent number
US06867198B2

Reaction notes

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