Cadaverine → HCID 12235402, compound

HRID 2117251Notes

Reaction equation

HRID 2117251 reaction equation
[CH2:1]([NH2:7])[CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].[C:8]1(=[O:14])[O:13][C:11](=[O:12])[CH2:10][CH2:9]1>CO.C(Cl)Cl>[NH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][NH:7][C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 273CadaverineHCID 7922Succinic anhydride

Product 1

HCID 12235402HCID 12235402, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,5-pentanediamine (2.5 g, 24 mmol) in dry methanol (20 mL), a solution of succinic acid anhydride (2 g, 20 mmol) in dry methylene chloride (20 mL) was added dropwise in 2 hrs, the product was precipitated as white solid and collected by filtration. Yield 80 %. 1H NMR (500 MHz, D2O, 25° C.) δ 1.280 (quint., J=7.5, 2H, CH2), 1.449 (quint., J=7.5, 2H, CH2), 1.577 (quint., J=7.5, 2H, CH2), 2.337 (s, 4H, CH2), 2.886 (t, J=7.5, 2H, CH2), 3.072 (t, J=7.5, 2H, CH2). 13C NMR (500 MHz, D2O, 25° C.) δ 22.73, 26.22, 27.66, 32.34, 33.13, 38.76, 39.37, 175.72, 180.90.

Workup

  1. customthe product was precipitated as white solid
  2. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e8f9afff053e4ceb92faa6262364f394
Source dataset
uspto-grants-2008_10
Patent number
US07442558B2

Reaction notes

Loading…