N,N-Diethylethylenediamine → (R/S)-N-[2-(diethylamino)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamid

HRID 1087075Notes

Reaction equation

HRID 1087075 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]([N:16]([CH2:20][CH3:21])[CH2:17][CH2:18][NH2:19])[CH3:15]>>[CH2:14]([N:16]([CH2:20][CH3:21])[CH2:17][CH2:18][NH:19][C:8](=[O:10])[CH2:7][N:4]1[CH2:5][CH2:6][CH:2]([OH:1])[C:3]1=[O:13])[CH3:15]

Participants

3

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 13385945ethyl (R/S)-2-(3-hydroxy-2oxo-1-pyrrolidinyl)acetate

Product 1

HCID 53697885(R/S)-N-[2-(diethylamino)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamid

Procedure

3.0 g of ethyl (R/S)-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetate and 3.7 g of 2-(diethylamino)ethylamine are heated to 95°-100° for 3.5 hours under nitrogen. The mixture is chromatographed on 45 g of aluminum oxide (neutral, activity grade III). The crude (R/S)-N-[2-(diethylamino)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide which is eluted with methylene chloride and ethyl acetate is again chromatographed on 25 g of aluminum oxide (neutral, activity grade III). The product which is eluted with ethyl acetate and ethanol is distilled in a bulb-tube at about 250°/0.03 mmHg.

Workup

  1. customThe mixture is chromatographed on 45 g of aluminum oxide (neutral, activity grade III)
  2. washThe crude (R/S)-N-[2-(diethylamino)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide which is eluted with methylene chloride and ethyl acetate
  3. customis again chromatographed on 25 g of aluminum oxide (neutral, activity grade III)
  4. washThe product which is eluted with ethyl acetate and ethanol
  5. distillationis distilled in a bulb-tube at about 250°/0.03 mmHg

Sources & evidence

ORD record
ord-af8d05cd5e034abb9f8ec4d9a38b043a
Source dataset
uspto-grants-1991_07
Patent number
US05034402

Reaction notes

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