Gamma-Butyrolactone → 1-(6-Aminohexyl)-2-pyrrolidinone

HRID 1955134Notes

Reaction equation

HRID 1955134 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].[C:9]1(=O)[O:13][CH2:12][CH2:11][CH2:10]1>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH2:11][C:12]1=[O:13]

Participants

3

Reactant 2

HCID 7302Gamma-ButyrolactoneHCID 16402Hexamethylenediamine

Product 1

HCID 211991301-(6-Aminohexyl)-2-pyrrolidinone

Procedure

Hexamethylenediamine (100 g, 0.86 mole) was heated with γ-butyrolactone (23.36 ml, 0.31 mole) at 210° C. under nitrogen for 24 hours in a three-neck reaction flask equipped with air reflux condenser. After the reaction, most of the unreacted diamine was crystallized upon cooling to room temperature; therefore, most of the excess diamine was filtered off. The remaining unreacted diamine in solution was vacuum distilled, then N-(6-aminohexyl)-2-pyrrolidone was obtained at 140° C. (0.9 torr) as a colorless liquid. Yield: 35 g (62%). Mass Spectra: m/e (relative intensity) 185(M+1+, 16.97).

Workup

  1. customequipped with air
  2. temperaturereflux condenser
  3. customAfter the reaction
  4. custommost of the unreacted diamine was crystallized
  5. filtrationtherefore, most of the excess diamine was filtered off
  6. distillationdistilled

Sources & evidence

ORD record
ord-63297025cddb404983e4f158a0bfe716
Source dataset
uspto-grants-2000_09
Patent number
US06124365

Reaction notes

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