(1-BOC-piperidin-4-yl)acetonitrile Chemical Properties

Boiling point:

344.3±15.0 °C(Predicted)

Density 

1.040±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-1.91±0.40(Predicted)

Appearance

White to light yellow Solid

Safety Information

HazardClass 

IRRITANT

HS Code 

2916399090

(1-BOC-piperidin-4-yl)acetonitrile Usage And Synthesis

Synthesis

The reaction was carried out with tert-butyl 4-((methylsulfonyl)oxymethyl)piperidine-1-carboxylate (15.3 g) and NaCN (4.00 g, 80.0 mmol) in a mixed solvent of EtOH (80 ml) and H2O (20 ml) with stirring for 24 hours at 80°C. After completion of the reaction, the solvent was removed by vacuum concentration. The residue was dissolved in AcOEt (300 ml) and H2O (100 ml) and the aqueous layer was extracted with AcOEt (300 ml). The organic layers were combined, washed with brine (100 ml), dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel column chromatography (eluent: hexane-AcOEt) to afford the target product 1-Boc-4-(cyanomethyl)piperidine (6.87 g, 76.6% yield) as a white solid.1H NMR (400 MHz, CDCl3) δ 1.21-1.31 (2H, m), 1.46 (9H, s), 1.78-1.86 (3H m), 2.31 (2H, d, J=6.4Hz), 2.64-2.78 (2H, m), 4.07-4.21 (2H, m).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3249 - 3253

(1-BOC-piperidin-4-yl)acetonitrile(256411-39-9)Related Product Information

• tert-Butyl 4-(cyanomethyl)-4-hydroxypiperidine-1-carboxylate
• (1-BOC-piperidin-4-yl)acetonitrile