tert-Butyl 4-(aminocarbothioyl)tetrahydropyridine-1(2H)-carboxylate Chemical Properties

Melting point:

130 °C

Boiling point:

356.0±52.0 °C(Predicted)

Density 

1.158±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

solid

pka

13.03±0.20(Predicted)

color 

White

Safety Information

Hazard Codes 

Xi,Xn,N

Risk Statements 

20/21/22-36/37/38-22-50

Safety Statements 

26-36/37/39-22-61

Hazard Note 

Irritant

HS Code 

2933399990

tert-Butyl 4-(aminocarbothioyl)tetrahydropyridine-1(2H)-carboxylate Usage And Synthesis

Synthesis

General procedure for the synthesis of tert-butyl 4-aminothiocarbonyltetrahydropyridine-1(2H)-carboxylate from tert-butyl 4-carbamoylpiperidine-1-carboxylate: tert-butyl 4-carbamoylpiperidine-1-carboxylate (2.65 g, 11.62 mmol) was dissolved in a solvent mixture of DME/DCM (2:1, 78 mL), followed by addition of Lawesson reagent (2.35 g, 5.81 mmol, 0.5 equiv). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and washed with saturated aqueous K2CO3 solution. The organic layer was separated, dried with anhydrous Na2SO4, filtered and concentrated to dryness. The obtained residue was ground with ether and dried to give tert-butyl 4-aminothiocarbonyltetrahydropyridine-1(2H)-carboxylate (2.65 g, 92% yield) as a white solid. The product was analyzed by HPLC showing a retention time (Rt) of 5.06 min. 1H NMR (401 MHz, DMSO-d6) δ ppm: 9.39 (br.s., 1H), 9.09 (br.s., 1H), 4.00 (d, J=12.6 Hz, 2H), 2.77-2.61 (m, 3H), 1.71-1.51 (m , 4H), 1.39 (br.s., 9H).

References

[1] Patent: WO2012/113774, 2012, A1. Location in patent: Page/Page column 40
[2] Patent: US2013/324551, 2013, A1. Location in patent: Paragraph 0311; 0312; 0313
[3] Patent: WO2011/153435, 2011, A1. Location in patent: Page/Page column 13-14
[4] Patent: US2011/318418, 2011, A1. Location in patent: Page/Page column 12
[5] Patent: WO2016/30443, 2016, A1. Location in patent: Page/Page column 102

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