Ethyl 4-piperidinecarboxylate Chemical Properties

Boiling point:

204 °C(lit.)

Density 

1.02 g/mL at 25 °C(lit.)

vapor pressure 

39.4Pa at 25℃

refractive index 

n20/D 1.459(lit.)

Flash point:

176 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Liquid

pka

9.83±0.10(Predicted)

color 

Clear colorless to slightly brown

Water Solubility 

miscible

BRN 

118419

InChI

InChI=1S/C8H15NO2/c1-2-11-8(10)7-3-5-9-6-4-7/h7,9H,2-6H2,1H3

InChIKey

RUJPPJYDHHAEEK-UHFFFAOYSA-N

SMILES

N1CCC(C(OCC)=O)CC1

LogP

1.15

CAS DataBase Reference

1126-09-6(CAS DataBase Reference)

NIST Chemistry Reference

Ethyl piperidine-4-carboxylate(1126-09-6)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

34-36/37/38

Safety Statements 

23-24/25-36-26

RIDADR 

UN2735

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29333999

MSDS

• Language:English Provider:Ethyl 4-piperidinecarboxylate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethyl 4-piperidinecarboxylate Usage And Synthesis

Chemical Properties

clear colorless to slightly brown liquid

Uses

Reactant for synthesis of:• ;SMN protein modulators1• ;β-aryl and β-amino-substituted aliphatic esters by rhodium catalyzed tandem double bond migration/conjugate addition2• ;Nitroethylenediamines by nucleophilic ring opening of nitroimidazolidinone3• ;RhoA inhibitors for cardiovascular disease therapy4• ;Saccharin derived Mannich bases as antimicrobials and antioxidants5Reactant for one-pot reductive amination and Suzuki-Miyaura cross coupling of formyl aryl and heteroaryl MIDA boronates6

Uses

Reactant for synthesis of SMN protein modulators and β-aryl and β-amino-substituted aliphatic esters by rhodium catalyzed tandem double bond migration/conjugate addition.

Uses

It is used as a reactant for synthesis of SMN protein modulators, β-aryl and β-amino-substituted aliphatic esters by rhodium catalyzed tandem double bond migration/conjugate addition, nitroethylenediamines by nucleophilic ring opening of nitroimidazolidinone. It is also involved in the reactions of RhoA inhibitors for cardiovascular disease therapy and saccharin derived Mannich bases as antimicrobials and antioxidants. It is employed as a reactant for one-pot reductive amination and Suzuki-Miyaura cross coupling of formyl aryl and heteroaryl MIDA boronates.

Synthesis Reference(s)

Tetrahedron Letters, 23, p. 193, 1982 DOI: 10.1016/S0040-4039(00)86783-0

Synthesis

1. 4-Piperidinecarboxylic acid (1.29 g, 10.0 mmol) was dissolved in anhydrous ethanol (50 mL). 2. The reaction solution was cooled to 0 °C and thionyl chloride (2.91 mL, 40.0 mmol) was added slowly and dropwise. 3. The reaction mixture was stirred and heated to reflux for 48 hours. 4. After completion of the reaction, the solvent was evaporated under reduced pressure to give a yellow oily crude product. 5. The crude product was dissolved in ethyl acetate (EtOAc) and washed with 10% sodium hydroxide (NaOH) solution. 6. The organic layer was separated, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give the clarified oily product ethyl 4-piperidinecarboxylate (1.48 g, 94% yield). 7. The product was analyzed by 1H NMR. 7. The product was characterized by 1H NMR (400 MHz, CDCl3) and mass spectrometry (ESI) to confirm the correct structure.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7106 - 7109
[2] Letters in Organic Chemistry, 2015, vol. 12, # 4, p. 277 - 279
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1983, vol. 22, # 5, p. 505
[4] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 18, p. 2693 - 2698
[5] European Journal of Medicinal Chemistry, 2000, vol. 35, # 7-8, p. 699 - 706

Ethyl 4-piperidinecarboxylate(1126-09-6)Related Product Information

• ETHYL 4-PIPERIDINECARBOXYLATE HYDROCHLORIDE,ETHYL 4-PIPERIDINECARBOXYLATE HCL
• Isonipecotic acid
• 1-PIPERIDINECARBONYL CHLORIDE
• 4-PIPERIDINECARBOXYLIC ACID T-BUTYL ESTER HCL
• Hexahydroisonicotinamide
• Methyl 4-piperidinecarboxylate
• 4-Piperidinemethanol
• 4,4-Piperidinediol hydrochloride
• Methyl isonipecotate
• 1-BENZYL-3-OXO-PIPERIDINE-4-CARBOXYLIC ACID ETHYL ESTER
• MEPERIDINE
• Ethyl 1-methyl-4-piperidinecarboxylate
• ETHYL 1-(2-CHLOROACETYL)-4-PIPERIDINECARBOXYLATE
• Ethyl 4-piperidinecarboxylate
• DIPHENOXYLATE HYDROCHLORIDE
• MEPERIDINE HYDROCHLORIDE
• Ethyl 4-(ethoxycarbonyl)piperidine-1-acetate
• Ethyl N-benzyl-3-oxo-4-piperidine-carboxylate hydrochloride