4-Cyanopiperidine

4-Cyanopiperidine Property

Melting point:

0°C

Boiling point:

0°C

Density 

0.987 g/mL at 25 °C

refractive index 

1.4755

Flash point:

0°C

storage temp. 

2-8°C

solubility 

Soluble in chloroform.

form 

Liquid

pka

9.26±0.10(Predicted)

color 

Colorless to pale yellow

InChI

InChI=1S/C6H10N2/c7-5-6-1-3-8-4-2-6/h6,8H,1-4H2

InChIKey

FSDNTQSJGHSJBG-UHFFFAOYSA-N

SMILES

N1CCC(C#N)CC1

CAS DataBase Reference

4395-98-6(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38-41-22

Safety Statements 

26-36/37/39-36-39

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

4-Cyanopiperidine Chemical Properties,Usage,Production

Chemical Properties

Yellowish-Orangish Oil

Uses

4-Cyanopiperidine is used as an intermediate for the preparation of pharmaceutical substances like antidepressants and anti-inflammatory. It is used as a precursor for the synthesis of piperidine derivatives.

Synthesis

The general procedure for the synthesis of 4-cyanopiperidine from N-Boc-4-cyanopiperidine is as follows: Step A: Preparation of 4-cyanopiperidine hydrochloride (mt17-1) N-Boc-4-cyanopiperidine (4.00 g, 19.0 mmol) was dissolved in 20 mL of 4M HCl/EtOAc solution and stirred at room temperature for 30 min. After completion of the reaction, the mixture was concentrated under vacuum to give 2.10 g of 4-cyanopiperidine hydrochloride (mt17-1) as a white solid in 100% yield. 1H-NMR (DMSO-d6) δ: 9.32 (br, 1H), 3.18-3.08 (m, 3H), 2.97-2.92 (m, 2H), 2.08-2.04 (m, 2H), 1.95-1.85 (m, 2H).

References

[1] Patent: WO2014/178, 2014, A1. Location in patent: Page/Page column 102
[2] Patent: WO2014/4416, 2014, A1. Location in patent: Page/Page column 102
[3] Patent: US2014/5103, 2014, A1. Location in patent: Paragraph 0459; 0460
[4] Patent: US2015/197531, 2015, A1. Location in patent: Paragraph 0460
[5] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 7, p. 822 - 829