Ethyl 4-piperidinecarboxylate

Base Information

• Chemical Name: Ethyl 4-piperidinecarboxylate
• CAS No.: 1126-09-6
• Molecular Formula: C8H15NO2
• Molecular Weight: 157.213
• Hs Code.: 29333999
• European Community (EC) Number: 214-416-7
• NSC Number: 93792
• DSSTox Substance ID: DTXSID90150109
• Nikkaji Number: J27.969B
• Wikidata: Q72475612
• ChEMBL ID: CHEMBL2251608
• Mol file: 1126-09-6.mol

Synonyms:1126-09-6;Ethyl piperidine-4-carboxylate;Ethyl 4-piperidinecarboxylate;Ethyl isonipecotate;Piperidine-4-carboxylic acid ethyl ester;4-Piperidinecarboxylic acid, ethyl ester;MFCD00006003;Isonipecotic Acid Ethyl Ester;Ethylisonipecotate;4-Piperidinecarboxylic Acid Ethyl Ester;4-Carbethoxypiperidine;4-Carboethoxypiperidine;Ethyl 4-Piperidinecarboxylate--d9;EINECS 214-416-7;ethylpiperidine-4-carboxylate;1219803-75-4;4-(Ethoxycarbonyl)piperidine;a-Ethyl isonipecotate;4-Ethoxycarbonylpiperidine;4-ethoxycarbonyl piperadine;4-ethoxycarbonyl piperidine;Ethyl isonipecotate, 98%;Oprea1_864652;SCHEMBL27886;ethyl piperid-4-ylcarboxylate;ethyl piperidin-4-carboxylate;ethyl 4-piperidine carboxylate;ethyl 4-piperidine-carboxylate;ethyl piperadine-4-carboxylate;ethyl piperdin-4-ylcarboxylate;ethyl piperidine 4-carboxylate;Ethyl-4-piperidine carboxylate;ethyl piperidin-4-ylcarboxylate;CHEMBL2251608;DTXSID90150109;piperidine-4-carboxylic acid ethyl;BCP27137;NSC93792;STR02241;BBL008541;NSC 93792;NSC-93792;STK260860;AKOS000119792;AC-2523;CS-W009052;PIPERIDINE-4-CARBOXYLATE, ETHYL;piperidine-4-carboxylic acid ethylester;piperidine-4carboxylic acid ethyl ester;SB42922;SDCCGMLS-0066232.P001;4-piperidine-carboxylic acid ethyl ester;SY001812;SY278371;TS-02094;AM20080077;FT-0600591;I0294;EN300-19517;P20835;W-108644;F2190-0332;Z104474100

Chemical Property of Ethyl 4-piperidinecarboxylate

Chemical Property:

• Appearance/Colour: clear colorless to slightly brown liquid
• Vapor Pressure: 0.27mmHg at 25°C
• Refractive Index: n20/D 1.459(lit.)
• Boiling Point: 204 °C at 760 mmHg
• PKA: 9.83±0.10(Predicted)
• Flash Point: 83.3 °C
• PSA: 38.33000
• Density: 1.003 g/cm³
• LogP: 0.87790
• Storage Temp.: Store below +30°C.
• Water Solubility.: miscible
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 157.110278721
• Heavy Atom Count: 11
• Complexity: 130

Purity/Quality:

99%, ^*data from raw suppliers

Ethyl isonipecotate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 23-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1CCNCC1
• 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 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. 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.

Technology Process of Ethyl 4-piperidinecarboxylate

There total 8 articles about Ethyl 4-piperidinecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

isonipecotic acid (498-94-2) + ethanol (64-17-5) → 4-carbethoxypiperidine (1126-09-6)

Guidance literature:

With thionyl chloride; at 0 ℃; for 48h; Reflux;

DOI:10.1016/j.bmcl.2012.09.080

Reference yield: 71.0%

1-acetyl-piperidine-4-carboxylic acid ethyl ester (69001-10-1) → 4-carbethoxypiperidine (1126-09-6)

Guidance literature:

1-acetyl-piperidine-4-carboxylic acid ethyl ester; With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -78 - 0 ℃; for 2h; Inert atmosphere;

With ethylmagnesium bromide; In diethyl ether; dichloromethane; at -78 ℃; for 2h; chemoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2015.04.074

Reference yield:

isonicotinic acid ethylester (1570-45-2) → 4-piperidinemethanol (6457-49-4) + 4-carbethoxypiperidine (1126-09-6)

Guidance literature:

With sodium; butan-1-ol;

upstream raw materials:

isonipecotic acid

isonicotinic acid ethylester

ethanol

butan-1-ol

Downstream raw materials:

1-(2-hydroxy-4,5-dimethyl-benzyl)-piperidine-4-carboxylic acid ethyl ester

ethyl 1-benzoyl-4-piperidine-carboxylate

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate

1-acetyl-piperidine-4-carboxylic acid ethyl ester

Refernces

• 1、 Li, Bing,Wang, Kaiyuan,Zhang, Rui,Li, Baihui,Shen, Yangli,Ji, Qinggang. "Design, synthesis and biological evaluation of novel diazaspiro[4.5]decan-1-one derivatives as potential chitin synthase inhibitors and antifungal agents". . . Retrieved 2019.
• 2、 Clark, Joseph R.,Dixon, Charlie F.,Feng, Kaibo,Han, Wei,Ide, Takafumi,Koch, Vanessa,Teng, Dawei,Wendell, Chloe I.,White, M. Christina. "Late-Stage Intermolecular Allylic C-H Amination". supporting information. p. 14969 - 14975. Retrieved 2021/10/01.
• 3、 Aguilar Troyano, Francisco José,Ballaschk, Frederic,Jaschinski, Marcel,?zkaya, Yasemin,Gómez-Suárez, Adrián. "Light-Mediated Formal Radical Deoxyfluorination of Tertiary Alcohols through Selective Single-Electron Oxidation with TEDA2+.". supporting information. p. 14054 - 14058. Retrieved 2019/11/11.