2-Pyrrolidone → N-(hydroxyethoxyethoxyethyl)pyrrolidine

HRID 1995553Notes

Reaction equation

HRID 1995553 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=O.Cl[CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH:14](O)[CH3:15].[OH-:17].[K+]>C(O)C>[OH:17][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 14797Potassium HydroxideHCID 183503572-Chloroethoxyethoxyethanol

Product 1

HCID 57119225N-(hydroxyethoxyethoxyethyl)pyrrolidineYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A total of 295 g of pyrrolidone and 250 g of 2-chloroethoxyethoxyethanol in 750 ml of ethanol was refluxed for 5 hours. The reaction mixture was then treated with 106 g of KOH and refluxed for an additional hour. Filtration and distillation yielded 229 g of N-(hydroxyethoxyethoxyethyl)pyrrolidine (b.p.=145° C. at 3 mm).

Workup

  1. temperaturerefluxed for an additional hour
  2. filtrationFiltration and distillation

Sources & evidence

ORD record
ord-022f33e858d94b358a17e7546382fa75
Source dataset
uspto-grants-1983_09
Patent number
US04405582

Reaction notes

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