Ethyl N-Boc-piperidine-4-carboxylate Chemical Properties

Boiling point:

120-135 °C/0.5 mmHg

Density 

1.046 g/mL at 25 °C

refractive index 

n20/D 1.458

Flash point:

>230 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform, Ethyl Acetate

pka

-2.23±0.40(Predicted)

form 

Liquid

color 

Clear colorless to pale yellow

InChI

InChI=1S/C13H23NO4/c1-5-17-11(15)10-6-8-14(9-7-10)12(16)18-13(2,3)4/h10H,5-9H2,1-4H3

InChIKey

MYHJCTUTPIKNAT-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(C(OCC)=O)CC1

CAS DataBase Reference

142851-03-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

Ethyl N-Boc-piperidine-4-carboxylate Usage And Synthesis

Chemical Properties

Liquid

Uses

Ethyl N-Boc-piperidine-4-carboxylate is used as a reagent to synthesize 3-amino-1-(5-indanyloxy)-2-propanol derivatives as sodium channel blockers to treat stroke patients. Ethyl N-Boc-piperidine-4-carboxylate is also used as a reagent to prepare inhibitors of tumour necrosis factor alpha-converting enzyme.

Uses

Substrate used in a palladium-catalyzed α-arylation of esters with heterocyclic bromides and chlorides leading to, for example, 4-pyridylpiperidinyl esters.

Synthesis

The general procedure for the synthesis of ethyl N-Boc-4-piperidinecarboxylate from di-tert-butyl dicarbonate was as follows: ethyl isopiperidinate (5.00 g, 0.032 mol) and triethylamine (4.9 mL, 0.035 mol) were dissolved in dichloromethane (25 mL) at 0 °C, and the dichloromethane of di-tert-butyl dicarbonate (7.2 g, 0.033 mol) was slowly added ( 25mL) solution. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, it was washed three times with potassium bisulfate solution and then once with brine. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated in vacuum to afford the target product ethyl N-Boc-4-piperidinecarboxylate (8.23 g, 100% yield) as a colorless oil. The structure of the product was confirmed by 1H NMR (C6D6,500MHz) δ 3.88 (q, J=7.5Hz, 2H), 2.52 (m, 1H), 1.60-1.48 (m, 8H), 1.42 (s, 9H), 0.92 (t, 3H) and mass spectra (280.44 (M+Na)+).

References

[1] Patent: US2004/204397, 2004, A1
[2] Patent: US2003/144302, 2003, A1
[3] Patent: US2002/55631, 2002, A1
[4] Patent: US2002/86887, 2002, A1
[5] Patent: US5716965, 1998, A

Ethyl N-Boc-piperidine-4-carboxylate(142851-03-4)Related Product Information

• BUTYL OLEATE
• Ethyl propionate
• Ethylparaben
• Buprofezin
• Cyclohexanecarboxylic acid ethyl ester
• Ethanol
• OXALIC ACID
• Ethyl formate
• Trinexapac-ethyl
• ISOXADIFEN-ETHYL
• Ethyl 4-piperidinecarboxylate
• Urethane
• Ethyl cyanoformate
• Ethyl nipecotate
• Ethyl acetate
• 2-Ethoxyethanol
• Isonipecotic acid
• Cyhalofop-butyl