Ethanolamine → N-[3-(2-hydroxyethylamino)propionyl]-3-[3-[1-(1-pyrrolidinyl)ethyl]phenoxy]propylamine

HRID 847743Notes

Reaction equation

HRID 847743 reaction equation
[N:1]1([CH:6]([C:8]2[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:20])[CH:17](Br)[CH3:18])[CH3:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:24]([CH2:26][NH2:27])[OH:25]>C(O)C>[OH:25][CH2:24][CH2:26][NH:27][CH2:18][CH2:17][C:16]([NH:15][CH2:14][CH2:13][CH2:12][O:11][C:10]1[CH:21]=[CH:22][CH:23]=[C:8]([CH:6]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH3:7])[CH:9]=1)=[O:20]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 20567120N-[3-[3-[1-(1-pyrrolidinyl)ethyl]phenoxy]propyl]bromopropionamide

Product 1

HCID 20567144N-[3-(2-hydroxyethylamino)propionyl]-3-[3-[1-(1-pyrrolidinyl)ethyl]phenoxy]propylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

500 mg of the amide compound obtained in step (A) was heated under reflux for 2 hours in 1 ml of ethanolamine and 1 ml of ethanol. The solvent was distilled off under reduced pressure, and potassium carbonate was added. The mixture was extracted with chloroform. The solvent was distilled off, and the residue was purified by TLC (developing solvent: chloroform/diethylamine=10:1) to afford 355 mg of N-[3-(2-hydroxyethylamino)propionyl]-3-[3-[1-(1-pyrrolidinyl)ethyl]phenoxy]propylamine.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, and potassium carbonate
  2. additionwas added
  3. extractionThe mixture was extracted with chloroform
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by TLC (developing solvent: chloroform/diethylamine=10:1)

Sources & evidence

ORD record
ord-87a3e3b29a9d4fe6835ac1ee6c6f1d93
Source dataset
uspto-grants-1981_10
Patent number
US04293557

Reaction notes

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