Ethylenediamine → N-[2-(amino)ethyl]-2-(3-hydroxy-2oxo-1-pyrrolidinyl)acetamide

HRID 1906271Notes

Reaction equation

HRID 1906271 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]([O:10]CC)=O)[C:3]1=[O:13].[CH2:14]([NH2:17])[CH2:15][NH2:16]>>[NH2:16][CH2:15][CH2:14][NH:17][C:8](=[O:10])[CH2:7][N:4]1[CH2:5][CH2:6][CH:2]([OH:1])[C:3]1=[O:13]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 13385945ethyl (R/S)-2-(3-hydroxy-2oxo-1-pyrrolidinyl)acetate

Product 1

HCID 19817649N-[2-(amino)ethyl]-2-(3-hydroxy-2oxo-1-pyrrolidinyl)acetamide

Procedure

A mixture of 3.5 g of ethyl (R/S)-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetate and 11.2 g of 1,2-ethylenediamine is left to stand at room temperature for 20 hours. The excess 1,2-ethylenediamine is evaporated in vacuo. The residue is dissolved in 40 ml of hot acetonitrile and stirred at room temperature for 2 hours and then in an ice-bath for 1 hour. By filtration there is isolated N-[2-(amino)ethyl]-2-(3-hydroxy-2oxo-1-pyrrolidinyl)acetamide of melting point 110°-112°.

Workup

  1. waitis left
  2. customThe excess 1,2-ethylenediamine is evaporated in vacuo
  3. dissolutionThe residue is dissolved in 40 ml of hot acetonitrile
  4. waitin an ice-bath for 1 hour
  5. filtrationBy filtration

Sources & evidence

ORD record
ord-b10d534f31004bb0800c48c358ca9f30
Source dataset
uspto-grants-1987_03
Patent number
US04650878

Reaction notes

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