(S)-3-(1-AMINOETHYL)BENZENAMINE Chemical Properties

Boiling point:

266.5±15.0 °C(Predicted)

Density 

1.056±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

9.06±0.10(Predicted)

(S)-3-(1-AMINOETHYL)BENZENAMINE Usage And Synthesis

Synthesis

General procedure for the synthesis of (S)-3-(1-aminoethyl)aniline from 1-(3-nitrophenyl)ethylamine: (1S)-1-(3-nitrophenyl)ethylamine (13.1 g, 79.4 mmol) was mixed with 10% palladium-carbon catalyst (0.75 g) in methanol (250 mL), and the reaction was carried out with vigorous stirring at atmospheric pressure under a hydrogen atmosphere for 19 hours. Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad and the diatomaceous earth pad was washed with methanol (800 mL). After combining the filtrates, the solvent was removed by concentration under reduced pressure to afford the target product (S)-3-(1-aminoethyl)aniline as a brown solid (10.8 g, 100% yield).

References

[1] Patent: WO2008/58341, 2008, A1. Location in patent: Page/Page column 91
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 4, p. 1206 - 1209
[3] Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 3, p. 408 - 419

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