2-(N,N-Dibenzyl)-amino-1,3-propanediol

2-(N,N-Dibenzyl)-amino-1,3-propanediol Property

Melting point:

81-82 °C(Solv: benzene (71-43-2); hexane (110-54-3))

Boiling point:

455.9±35.0 °C(Predicted)

Density 

1.154±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

14.15±0.10(Predicted)

Appearance

White to light yellow Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-(N,N-Dibenzyl)-amino-1,3-propanediol Chemical Properties,Usage,Production

Synthesis

To a solution of 2-amino-1,3-propanediol (S2, 299 mg, 3.28 mmol, 1.0 eq.) in acetonitrile (MeCN, 10 mL) was added potassium carbonate (K2CO3, 2.27 g, 16.4 mmol, 5.0 eq.) and benzyl bromide (0.98 mL, 1.4 g, 8.3 mmol, 2.5 eq.). The reaction mixture was stirred at room temperature for 18 h and subsequently diluted with water (10 mL). The aqueous layer was extracted with ethyl acetate (EtOAc, 3 x 10 mL) and the combined organic phases were dried over anhydrous sodium sulfate (Na2SO4). The solvent was removed by concentration under reduced pressure and the residue was purified by silica gel column chromatography (SiO2, petroleum ether/ethyl acetate 1:1) to afford 2-(N,N-dibenzyl)amino-1,3-propanediol (S3, 716 mg, 2.64 mmol, 80% yield) as a white solid. Thin Layer Chromatography (TLC) Rf 0.20 (petroleum ether/ethyl acetate 1:1); melting point 113°C; 1H NMR (300 MHz, C6D6) δ: 2.30 (bs, 2H, OH), 2.93 (tt, 1H, J = 7.5, 5.9 Hz, 2-H), 3.37 (dd, 2H, J = 10.8, 5.9 Hz, 1-Ha, 3- Ha), 3.48 (dd, 2H, J = 10.8, 7.5 Hz, 1-Hb, 3-Hb), 3.53-3.66 (m, 4H, CH2Ph), 7.01-7.32 (m, 10H, Ph-H); 13C NMR (76 MHz, C6D6) δ: 54.4, 60.2, 60.3, 127.4, 128.7, 129.2, 140.1; infrared spectra (ATR) ν: 3245, 1493, 1451, 1049, 1025, 999, 741, 730, 695 cm-1; UV spectra (MeCN) λmax (logε): 206 (4.28), 259 (2.77) nm; mass spectra (ESI+) m/z: 272.2 (M + H+), 294.2 (M + Na+); high-resolution mass spectrometry (ESI+) m/z: C17H21NNaO2 294.1465 (M + Na+) calculated, 294.1466 measured.

References

[1] Journal of Organic Chemistry, 2012, vol. 77, # 21, p. 9641 - 9651
[2] European Journal of Organic Chemistry, 2008, # 1, p. 53 - 63
[3] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 1, p. 186 - 193
[4] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1135 - 1142
[5] Chemistry - A European Journal, 2018, vol. 24, # 60, p. 16136 - 16148