Piperazine, 1-[(6-broMo-3-pyridinyl)Methyl]-4-ethyl- Chemical Properties

Boiling point:

365.4±37.0 °C(Predicted)

Density 

1.328±0.06 g/cm3(Predicted)

storage temp. 

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

pka

7.67±0.10(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C12H18BrN3/c1-2-15-5-7-16(8-6-15)10-11-3-4-12(13)14-9-11/h3-4,9H,2,5-8,10H2,1H3

InChIKey

DMNPLEDMMNWHTL-UHFFFAOYSA-N

SMILES

N1(CC2=CC=C(Br)N=C2)CCN(CC)CC1

Piperazine, 1-[(6-broMo-3-pyridinyl)Methyl]-4-ethyl- Usage And Synthesis

Synthesis

To 100 mL of anhydrous dichloromethane (DCM) were added N-ethylpiperazine (10 g, 54 mmol) and 2-bromo-5-formylpyridine (6.20 g, 54.00 mmol) followed by batchwise addition of sodium triacetoxyborohydride (NaHB(OAc)3, 17.20 g, 81.00 mmol). The reaction mixture was stirred at room temperature for 5 hours. Upon completion of the reaction, the mixture was diluted with DCM (100 mL) and the pH was adjusted to 8-10 by adding saturated sodium carbonate (Na2CO3) solution. the mixture was partitioned between water and dichloromethane. The aqueous phase was extracted twice with dichloromethane. The organic phases were combined, washed sequentially with water and brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated in vacuum. The crude product was purified by silica gel column chromatography (eluent: DCM/MeOH = 50:1) to afford the target compound 1-((6-bromopyridin-3-yl)methyl)-4-ethylpiperazine (8a, 14.00 g, 92.00% yield) as a yellow solid. Mass spectrum (ESI): calculated value C12H18BrN3 [M+H]+ 284, measured value 284.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 5, p. 974 - 978
[2] Patent: CN105622638, 2016, A. Location in patent: Paragraph 0220
[3] Patent: CN106608879, 2017, A. Location in patent: Paragraph 0142-0145
[4] European Journal of Medicinal Chemistry, 2018, vol. 144, p. 1 - 28
[5] Journal of Medicinal Chemistry, 2017, vol. 60, # 5, p. 1892 - 1915

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