Succinic anhydride → HCID 5138283, compound

HRID 1374581Notes

Reaction equation

HRID 1374581 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH3:8][N:9]([CH3:13])[CH2:10][CH2:11][NH2:12].O1CCOCC1>C(C(C)=O)C>[CH3:8][N:9]([CH3:13])[CH2:10][CH2:11][NH:12][C:1](=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 312751,4-DioxaneHCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 5138283HCID 5138283, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

1.4 g of succinic anhydride and then 1.5 cm3 of 2-dimethylaminoethylamine are added to 15 cm3 of dioxane. After stirring for 18 hours at room temperature, the solvent is evaporated under reduced pressure (2.7 kPa) at 20° C., to give a residue which is taken up hot in 40 cm3 of methyl ethyl ketone. After cooling, the solubilized fraction is removed. The residual gum is crystallized hot from 15 cm3 of acetone. After filtration, the solid is rinsed with a minimum of acetone and then with diethyl ether, and dried under reduced pressure (2.7 kPa) at 20° C. to give 2.03 g of N-(2-dimethylaminoethyl)succinamic acid in the form of a white solid melting at 155° C.

Workup

  1. customthe solvent is evaporated under reduced pressure (2.7 kPa) at 20° C.
  2. customto give a residue which
  3. temperatureAfter cooling
  4. customthe solubilized fraction is removed
  5. customThe residual gum is crystallized hot from 15 cm3 of acetone
  6. filtrationAfter filtration
  7. washthe solid is rinsed with a minimum of acetone
  8. dry with materialwith diethyl ether, and dried under reduced pressure (2.7 kPa) at 20° C.

Sources & evidence

ORD record
ord-95095452ddd3499199b8f218d05f93b4
Source dataset
uspto-grants-2007_01
Patent number
US07166594B2

Reaction notes

Loading…