N-Boc-3-Cyanopiperidine Chemical Properties

Melting point:

60-65℃

Boiling point:

40°C/30mmHg(lit.)

Density 

1.07±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

soluble in Methanol

pka

-3.42±0.40(Predicted)

form 

Powder

color 

White to yellow

Sensitive 

Moisture Sensitive

InChI

InChI=1S/C11H18N2O2/c1-11(2,3)15-10(14)13-6-4-5-9(7-12)8-13/h9H,4-6,8H2,1-3H3

InChIKey

UEFZTXGFHKPSFS-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCCC(C#N)C1

CAS DataBase Reference

91419-53-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-36/37/38-50

Safety Statements 

26-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29335990

N-Boc-3-Cyanopiperidine Usage And Synthesis

Uses

N-Boc-3-Cyanopiperidine is an intermediate used to prepare inhibitors of aurora kinases based on the imidazo-[1,2-a]-Pyrazine core.

Synthesis

General procedure for the synthesis of tert-butyl 3-cyanopiperidine-1-carboxylate (3) from N-BOC-3-piperidinecarboxamide: To a solution of tert-butyl-3-carbamoylpiperidine-1-carboxylate (2) (1.0 g, 4 mmol) in anhydrous methylene chloride (20 mL) was added triethylamine (3.1 g, 31.0 mmol), followed by a slow, dropwise addition of trifluoroacetic acid anhydride (4.1 g , 20.0 mmol). The reaction mixture was gradually warmed to room temperature and stirred continuously for 16 hours. Upon completion of the reaction, the mixture was partitioned between dichloromethane (50 mL) and water (50 mL). The organic phase was washed with saturated sodium bicarbonate solution (100 mL) and subsequently dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure to give a viscous liquid product 3 (800 mg, 87% yield).1H NMR (400 MHz, CDCl3) δ 1.49 (s, 9H), 1.77 (m, 2H), 1.97 (brs, 1H), 2.66 (m, 1H), 3.35-3.84 (brs, 4H).

References

[1] Patent: US2009/215822, 2009, A1. Location in patent: Page/Page column 11
[2] Patent: WO2006/123257, 2006, A2. Location in patent: Page/Page column 34
[3] Journal of the American Chemical Society, 2018, vol. 140, # 5, p. 1627 - 1631
[4] Tetrahedron, 2002, vol. 58, # 18, p. 3561 - 3577
[5] Patent: WO2014/149164, 2014, A1. Location in patent: Paragraph 00606

N-Boc-3-Cyanopiperidine(91419-53-3)Related Product Information

• ETHYL 2-CYANOACRYLATE
• Methylene dithiocyanate
• Haloperidol
• Sodium cyanoborohydride
• DROPERIDOL
• tert-butyl 3-bromoazetidine-1-carboxylate
• 1-Boc-3-Cyanoazetidine
• 1-Boc-3-pyrrolidinecarbaldehyde
• 4-N-Boc-2-cyanopiperidine
• DI-TERT-BUTYL ETHER
• 1-Boc-4-cyanopiperidine
• (S)-1-N-BOC-3-CYANO-PIPERIDINE
• (S)-1-N-Boc-3-cyanopiperidine
• (R)-1-N-BOC-3-CYANO-PIPERIDINE
• 3-CYANO-4-OXO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• Diphenoxylate
• 1-Boc-2-cyanopiperidine
• TERT-BUTYL N-(2-CYANOETHYL)CARBAMATE