4-THIOCARBAMOYL-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Chemical Properties

Boiling point:

354.7±52.0 °C(Predicted)

Density 

1.214±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

16.15±0.20(Predicted)

Appearance

light yellow solid

CAS DataBase Reference

196811-66-2

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

4-THIOCARBAMOYL-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Usage And Synthesis

Synthesis

To a solution of N-Boc-piperazine (5.0 g, 26.88 mmol) in anhydrous THF (50 mL) was added N,N'-thiocarbonyl diimidazole (5.48 g, 29.56 mmol) at room temperature and the reaction was stirred for 2 hours. Subsequently, the reaction mixture was heated to 50 °C for 1 hour. Upon completion of the reaction, the mixture was cooled to 0 °C and methanol ammonia solution (50 mL, 7 N) was slowly added. The resulting mixture was stirred at 60 °C for 20 hours. At the end of the reaction, the reaction mixture was diluted with water and extracted with EtOAc. The organic layers were combined and dried with anhydrous Na2SO4 and subsequently concentrated under vacuum. The crude product was purified by fast chromatography to afford the target compound 4-Boc-piperazine-1-thioamide. Yield: 4.0 g (92% yield) as a white solid.1H NMR (400 MHz, DMSO-d6) δ: 9.2 (m, 2H), 3.16-3.14 (m, 2H), 2.49-2.48 (m, 6H), 1.30 (s, 9H). lcms (method A): 246.2 (M + H), retention time 2.93 min. Purity 95.3% (max).

References

[1] Patent: WO2016/30443, 2016, A1. Location in patent: Page/Page column 106
[2] Patent: WO2017/144637, 2017, A1. Location in patent: Page/Page column 39
[3] Patent: US2010/197703, 2010, A1. Location in patent: Page/Page column 77
[4] Patent: WO2015/48662, 2015, A2. Location in patent: Page/Page column 105
[5] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 4, p. 1613 - 1631

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