N,N'-Dibenzyl-1,3-propanediamine Chemical Properties

Boiling point:

124 °C(Press: 0.55 Torr)

Density 

1.017±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

9.73±0.19(Predicted)

form 

Oil

color 

Clear Pale Yellow

N,N'-Dibenzyl-1,3-propanediamine Usage And Synthesis

Uses

N,N''-Dibenzyl-1,3-diaminopropane is a hepatitis C virus inhibitor.

Synthesis

General procedure for the synthesis of N,N'-dibenzylidene-1,3-propanediamine from N1,N3-dibenzylidene-1,3-propanediamine: N1,N3-dibenzylidene-1,3-propanediamine (1 eq.) was dissolved in methanol (50 mL), followed by the addition of sodium borohydride (NaBH4, 2 eq.) into a reaction vessel in a portion of the reaction. The reaction mixture was heated to reflux for 15 minutes. Upon completion of the reaction, it was cooled to room temperature and quenched by the slow addition of water (70 mL). The water phase was extracted with dichloromethane (3 x 50 mL). The organic phases were combined, dried with anhydrous potassium carbonate (K2CO3) and concentrated under reduced pressure to remove the solvent to give the target product N,N'-dibenzyl-1,3-propanediamine.

References

[1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2016, vol. 71, # 6, p. 667 - 676
[2] Tetrahedron Letters, 1998, vol. 39, # 47, p. 8645 - 8646
[3] Journal of Organic Chemistry, 2007, vol. 72, # 10, p. 3790 - 3799
[4] European Journal of Medicinal Chemistry, 2013, vol. 70, p. 315 - 325
[5] Zhurnal Obshchei Khimii, 1957, vol. 27, p. 526,528; engl. Ausg. S. 595

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