Description
Amino-PEG1-Amine is a water soluble PEG linker containing two amino groups. The amino groups are reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc.
Synthesis
General procedure for the synthesis of 2,2'-oxydiethylamine from 2,2'-(oxybis(ethane-2,1-diyl))bis(isoindoline-1,3-dione): the raw material (575 mg, 0.83 mmol) was mixed with 80% hydrazine hydrate (8.3 mmol) in chloroform (10 mL) with reflux stirring for 4 hours. After completion of the reaction, the reaction mixture was treated with water and extracted with chloroform. The organic layer was dried with magnesium sulfate followed by evaporation of the solvent. Purification by distillation afforded the target product 2,2'-oxy diethylamine (9a) in 93% yield; boiling point 75-79°C/5 mmHg (literature value 31: 55-60°C/2 mmHg). The structure of the product was confirmed by 1H NMR (500 MHz, DMSO-d6) δ 8.31 (4H, br s), 3.32 (4H, t, J = 5.5 Hz), 2.63 (4H, t, J = 5.5 Hz); 13C NMR (500 MHz, DMSO-d6) δ 72.7, 41.3; and mass spectrum (FAB) m/z: 105 [ M + H] for confirmation.
References
[1] Tetrahedron, 2016, vol. 72, # 29, p. 4258 - 4272
[2] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1982, vol. 18, # 2, p. 193 - 196
[3] Khimiya Geterotsiklicheskikh Soedinenii, 1982, # 2, p. 246 - 249
[4] Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 1124 - 1129
[5] Zhurnal Organicheskoi Khimii, 1980, vol. 16, # 6, p. 1301 - 1307
