Potassium Hydroxide → N-(hydroxyethoxyethoxyethyl)pyrrolidine

HRID 34715Notes

Reaction equation

HRID 34715 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH:13](O)[CH3:14].[OH-:16].[K+]>C(O)C>[OH:16][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 31268PyrrolidineHCID 183503572-Chloroethoxyethoxyethanol

Product 1

HCID 57119225N-(hydroxyethoxyethoxyethyl)pyrrolidineYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A total of 295 g of pyrrolidine 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-1ee06e1127574b56afdc6df850dc1086
Source dataset
uspto-grants-1988_08
Patent number
US04762934

Reaction notes

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