1-BOC-4-(CYANOACETYL)PIPERIDINE Chemical Properties

Boiling point:

365.0±32.0 °C(Predicted)

Density 

1.117±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

9.36±0.20(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C13H20N2O3/c1-13(2,3)18-12(17)15-8-5-10(6-9-15)11(16)4-7-14/h10H,4-6,8-9H2,1-3H3

InChIKey

VSLLBQBSHAGKLC-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(C(CC#N)=O)CC1

Safety Information

HS Code 

2924190090

1-BOC-4-(CYANOACETYL)PIPERIDINE Usage And Synthesis

Synthesis

GENERAL STEPS: Potassium tert-butoxide (69 g, 616 mmol) was added batchwise to a mixed solution of tetrahydrofuran (1 L) and acetonitrile (53 mL, 1027 mmol) of methyl 1-tert-butyloxycarbonyl-4-piperidinecarboxylate (50 g, 206 mmol) under ice-bath cooling conditions. The reaction mixture was gradually warmed to room temperature and stirred for 1 hour. Subsequently, the reaction mixture was slowly poured into saturated aqueous ammonium chloride solution (2 L) to terminate the reaction. The aqueous phase was extracted with ethyl acetate (3 x 500 mL) and the organic phase was combined. The organic phase was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the light yellow oily product tert-butyl 4-(2-cyanoacetyl)piperidine-1-carboxylate (40 g, 77% yield). The product was detected by thin layer chromatography (TLC) with the unfolding agent ratio of petroleum ether/ethyl acetate=2:1 and Rf value of 0.5.

References

[1] Patent: WO2014/111496, 2014, A1. Location in patent: Page/Page column 153
[2] Patent: EP3287463, 2018, A1. Location in patent: Paragraph 0225; 0226
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 20, p. 8182 - 8199
[4] Patent: WO2016/138532, 2016, A1. Location in patent: Paragraph 0251

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