1,2-Ethanediamine, N1,N1-bis(1-methylethyl)- → 1-Pyrrolidineacetamide, N-(2-(bis(1-methylethyl)amino)ethyl-3-hydroxy-2-oxo-, (+-)-

HRID 1906268Notes

Reaction equation

HRID 1906268 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].[CH:14]([N:17]([CH:21]([CH3:23])[CH3:22])[CH2:18][CH2:19][NH2:20])([CH3:16])[CH3:15]>>[CH:14]([N:17]([CH:21]([CH3:23])[CH3:22])[CH2:18][CH2:19][NH:20][C:8](=[O:10])[CH2:7][N:4]1[CH2:5][CH2:6][CH:2]([OH:1])[C:3]1=[O:13])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 84591,2-Ethanediamine, N1,N1-bis(1-methylethyl)-HCID 13385945ethyl (R/S)-2-(3-hydroxy-2oxo-1-pyrrolidinyl)acetate

Product 1

HCID 30698361-Pyrrolidineacetamide, N-(2-(bis(1-methylethyl)amino)ethyl-3-hydroxy-2-oxo-, (+-)-

Procedure

4.5 g of ethyl (R/S)-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetate are heated to 100° under nitrogen for 3.5 hours with 6.1 g of 2-(diisopropylamino)ethylamine. The crude product is chromatographed on aluminium oxide (neutral, activity grade III). With ethyl acetate/ethanol (1:1) and with ethanol there is eluted (R/S)-N-[2-(diisopropylamino)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide. After stirring in diethyl ether this has a melting point of 91°-93°; boiling point 230°-250°/0.01 mmHg (bulb-tube).

Workup

  1. customThe crude product is chromatographed on aluminium oxide (neutral, activity grade III)
  2. washWith ethyl acetate/ethanol (1:1) and with ethanol there is eluted (R/S)-N-[2-(diisopropylamino)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide

Sources & evidence

ORD record
ord-e02f068de0f540b0b8fae2c25c9191f0
Source dataset
uspto-grants-1987_03
Patent number
US04650878

Reaction notes

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