1-Boc-4-cyanopiperidine Chemical Properties

Melting point:

60-63 °C

Boiling point:

325.3±35.0 °C(Predicted)

Density 

1.07±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform

pka

-3.08±0.40(Predicted)

form 

Crystalline Powder

color 

White to off-white

InChI

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

InChIKey

UQADQTBQNVARAP-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

91419-52-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

20/21/22-50-36-22

Safety Statements 

36-36/37/39-61-26

RIDADR 

3439

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

1-Boc-4-cyanopiperidine Usage And Synthesis

Chemical Properties

Yellowish Oil

Uses

Reactant for synthesis of:

• Aminomethylated fluoropiperidines
• Protein kinase B inhibitors
• GlyT1 inhibitors
• Piperidinecarboxylic acids via nitrilase-catalyzed enantioselective synthesis

• Replacement in CB2 receptor inhibitors
• Double addition reactions of methyllithium and n-butyllithium to unsaturated nitriles

Synthesis

The general procedure for the synthesis of N-Boc-4-cyanopiperidine from tert-butyl 4-carbamoylpiperidine-1-carboxylate is as follows: to a solution of ethyl acetate (EtOAc, 1 mL, 1 M) containing an aldoxime or amide (1.0 mmol) and triethylamine (Et3N, 1.5 mmol) was added batchwise to XtalFluor-E (1.1 mmol) at room temperature. ). The reaction mixture was stirred at room temperature for 1 hour. Subsequently, the reaction was quenched with saturated sodium bicarbonate (NaHCO3) solution and extracted with aqueous sodium carbonate (Na2CO3) and dichloromethane (CH2Cl2, 2 × 10 mL). The combined organic layers were washed sequentially with water and brine, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure to give the crude product. If necessary, the crude product can be purified by fast column chromatography.

References

[1] Synthesis (Germany), 2015, vol. 47, # 23, p. 3758 - 3766
[2] Patent: WO2004/2483, 2004, A1. Location in patent: Page/Page column 21-22; 39-40
[3] Chemistry of Heterocyclic Compounds, 2009, vol. 45, # 12, p. 1503 - 1507
[4] European Journal of Medicinal Chemistry, 1984, vol. 19, # 2, p. 181 - 186
[5] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 7, p. 822 - 829

1-Boc-4-cyanopiperidine(91419-52-2)Related Product Information

• Butyl acetate
• Cyhalofop-butyl
• RESMETHRIN
• Haloperidol
• tert-Butanol
• Diisobutyl phthalate
• 4-Cyanopiperidine
• Methyl cyanoformate
• Isobutyl chloroformate
• tert-Butyl carbazate
• Methylene dithiocyanate
• Buprofezin
• Sodium cyanoborohydride
• 2-Butoxyethanol
• ETHYL 2-CYANOACRYLATE
• tert-Butyl peroxybenzoate
• Ethyl cyanoformate
• Butyl acrylate