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2-(1H-indol-3-yl)-2-methylpropan-1-amine

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2-(1H-indol-3-yl)-2-methylpropan-1-amine Basic information

Product Name:
2-(1H-indol-3-yl)-2-methylpropan-1-amine
Synonyms:
  • 2-(1H-indol-3-yl)-2-methylpropan-1-amine
  • 1H-Indole-3-ethanaMine, b,b-diMethyl-
  • 3-(2-Amino-tert-butyl)indole
  • beta,beta-Dimethyltryptamine
  • 1H-Indole-3-ethanamine, β,β-dimethyl-
CAS:
15467-31-9
MF:
C12H16N2
MW:
188.27
Mol File:
15467-31-9.mol
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2-(1H-indol-3-yl)-2-methylpropan-1-amine Chemical Properties

Boiling point:
347.3±17.0 °C(Predicted)
Density 
1.093
storage temp. 
under inert gas (nitrogen or Argon) at 2–8 °C
pka
17.31±0.30(Predicted)
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2-(1H-indol-3-yl)-2-methylpropan-1-amine Usage And Synthesis

Synthesis

23078-29-7

15467-31-9

2-(1H-indol-3-yl)-2-methylpropionitrile (1.8 g, 9.8 mmol) was dissolved in tetrahydrofuran (4 mL) at 25 °C, followed by the addition of methanol (10 mL) and Ruanne nickel catalyst (200 mg). The reaction was carried out under hydrogen pressure of 2.2 MPa for 72 hours. Upon completion of the reaction, the reaction was stopped and filtration was performed. The filtrate was concentrated by rotary evaporation under reduced pressure and subsequently purified by column chromatography with an eluent ratio of dichloromethane/methanol (v/v) = 20/1, which ultimately afforded the target product 2-(1H-indol-3-yl)-2-methyl-1-propanamine as a light yellow oil (1.58 g, 86% yield).

References

[1] Patent: CN104496987, 2016, B. Location in patent: Paragraph 0217; 0218; 0219; 0220
[2] Patent: CN104529865, 2017, B. Location in patent: Paragraph 0164; 0178; 0179
[3] Patent: WO2004/19935, 2004, A1. Location in patent: Page/Page column 67
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 4, p. 904 - 907

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