Ethanol → N-[3-[3-[1-(1-pyrrolidinyl)ethyl]phenoxy]propyl]hydroxypropionamide

HRID 847739Notes

Reaction equation

HRID 847739 reaction equation
[N:1]1([CH:6]([C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH3:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.O[CH2:20][CH2:21][C:22]([OH:24])=O.C1(N=C=NC2CCCCC2)CCCCC1.C([OH:42])C>C(Cl)(Cl)Cl>[N:1]1([CH:6]([C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:22](=[O:24])[CH:21]([OH:42])[CH3:20])[CH3:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 681523-Hydroxypropionic acidHCID 130179203-[3-[1-(1-Pyrrolidinyl)ethyl]phenoxy]propylamine

Product 1

HCID 20567133N-[3-[3-[1-(1-pyrrolidinyl)ethyl]phenoxy]propyl]hydroxypropionamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

240 mg of 3-[3-[1-(1-pyrrolidinyl)ethyl]phenoxy]propylamine was dissolved in 4.5 ml of chloroform, and a solution of 144 mg of 3-hydroxypropionic acid in 0.5 ml of ethanol was added, followed by further addition of 300 mg of dicyclohexylcarbodiimide. The mixture was stirred at room temperature for 6 hours, and the solvent was distilled off under reduced pressure. The residue was purified by TLC (developing solvent: chloroform/methanol=9/l) to afford 180 mg of N-[3-[3-[1-(1-pyrrolidinyl)ethyl]phenoxy]propyl]hydroxypropionamide as an oil.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe residue was purified by TLC (developing solvent: chloroform/methanol=9/l)

Sources & evidence

ORD record
ord-32daf5430fc74b4da6d79cd4688df297
Source dataset
uspto-grants-1981_10
Patent number
US04293557

Reaction notes

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