Gamma-Butyrolactone → 1,1'-Hexamethylenebis(pyrrolidin-2-one)

HRID 1649073Notes

Reaction equation

HRID 1649073 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].[C:9]1(=[O:14])O[CH2:12][CH2:11][CH2:10]1>>[N:1]1([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:14])[CH2:12][CH2:11][CH2:10][C:9]1=[O:14]

Participants

3

Reactant 2

HCID 7302Gamma-ButyrolactoneHCID 16402Hexamethylenediamine

Product 1

HCID 1187291,1'-Hexamethylenebis(pyrrolidin-2-one)

Procedure

11.62 g (0.1 M) of 1,6-diaminohexane and 21.66 g (0.25 M) of γ-butyrolactone were mixed and heated to 150°-165° for 22 hours. Excess γ-butyrolactone was then distilled off at reduced pressure (80°/2 mm). The light brown residue was poured into a crystallization dish where it immediately solidified. The solid was taken in chloroform, powdered, filtered and the tan powder was washed with chloroform. Yield 22.0 g (87%); melting point 101°-103°.

Workup

  1. temperatureheated to 150°-165° for 22 hours
  2. distillationExcess γ-butyrolactone was then distilled off at reduced pressure (80°/2 mm)
  3. additionThe light brown residue was poured into a crystallization dish where it
  4. filtrationfiltered
  5. washthe tan powder was washed with chloroform

Sources & evidence

ORD record
ord-41542d4fa9b347edaabd43b68daa1d47
Source dataset
uspto-grants-1983_11
Patent number
US04415563

Reaction notes

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