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

HRID 1066285Notes

Reaction equation

HRID 1066285 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-dc4a9e641b8949eb931a1a0f4b4b995c
Source dataset
uspto-grants-2001_06
Patent number
US06242500B1

Reaction notes

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