4-Cyanopiperidine Chemical Properties

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 Information

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

4-Cyanopiperidine Usage And Synthesis

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

4-Cyanopiperidine(4395-98-6)Related Product Information

• ETHYL 2-CYANOACRYLATE
• DROPERIDOL
• Haloperidol
• Methylene dithiocyanate
• Diphenoxylate
• 4-CYANOQUINUCLIDINE
• 1-BENZYL-4-CYANO-4-HYDROXYPIPERIDINE
• 4-ANILINO-1-BENZYL-4-CYANOPIPERIDINE
• 4-CYANO-4-PHENYLPIPERIDINE HYDROCHLORIDE
• 1-Benzyl-4-cyano-4-phenylpiperidine hydrochloride
• 1-CBZ-3-CYANOPIPERIDINE,BENZYL-3-CYANOPIPERIDINE-1-CARBOXYLATE
• (S) 2-CYANOPIPERIDINE,2-CYANOPIPERIDINE
• 1-Cyanopiperidine,N-CYANOPIPERIDINE
• TERT-BUTYL 4-CYANOPIPERIDINE-1-CARBOXYLATE,Boc-4-cyanopiperidine,1-BOC-4-CYANOPIPERIDINE,4-CYANOPIPERIDINE, N-BOC PROTECTED
• (R)-1-N-BOC-3-CYANO-PIPERIDINE
• 4-CYANOPIPERIDINE HCL
• 1-Boc-2-cyanopiperidine
• 1-N-BOC-3-CYANOPIPERIDINE,TERT-BUTYL-3-CYANOPIPERIDINE-1-CARBOXYLATE,1-Boc-3-cyanopiperidine