3,5-Dimethyl-piperazine-1-carboxylic acid tert-butyl ester Chemical Properties

Boiling point:

279.7±15.0 °C(Predicted)

Density 

0.970±0.06 g/cm3(Predicted)

storage temp. 

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

pka

8.58±0.60(Predicted)

Appearance

Off-white to light yellow Solid

CAS DataBase Reference

639068-43-2

3,5-Dimethyl-piperazine-1-carboxylic acid tert-butyl ester Usage And Synthesis

Synthesis

General procedure for the synthesis of 1-Boc-3,5-dimethylpiperazine from di-tert-butyl dicarbonate and 2,6-dimethylpiperazine: 2,6-dimethylpiperazine (200.0 mg, 1.75 mmol) and triethylamine (TEA, 0.6 mL, 4.37 mmol) were dissolved in dichloromethane (DCM, 6.0 mL), and di-tert-butyl dicarbonate (DTBD, 1.5 mmol, 2.6 mL) was added slowly at 0 °C. butyl dicarbonate ((Boc)2O, 458.7 mg, 2.10 mmol) was added slowly at 0 °C. The reaction mixture was stirred at room temperature for 12 hours and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent ratio: DCM:MeOH = 95:5). The fraction containing the target product was collected and evaporated to give tert-butyl 3,5-dimethylpiperazine-1-carboxylate (210.0 mg, 56% yield) as a yellow liquid.1H-NMR (300 MHz, CDCl3) δ: 3.95 (m, 2H), 2.79 (m, 2H), 2.33 (m, 2H), 1.46 (s, 9H), 1.07 (d. 6H, J = 6.3 Hz).

References

[1] Patent: US2005/54850, 2005, A1
[2] Patent: US2014/315888, 2014, A1. Location in patent: Paragraph 0558-0559
[3] Patent: US6235731, 2001, B1
[4] Patent: EP2154135, 2010, A1. Location in patent: Page/Page column 16
[5] Patent: US2010/160323, 2010, A1. Location in patent: Page/Page column 27-28

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