1-Boc-4-cyanopiperidine

Base Information

• Chemical Name: 1-Boc-4-cyanopiperidine
• CAS No.: 91419-52-2
• Molecular Formula: C11H18N2O2
• Molecular Weight: 210.276
• Hs Code.: 29333990
• European Community (EC) Number: 624-826-1
• DSSTox Substance ID: DTXSID10363890
• Nikkaji Number: J2.766.911E
• Wikidata: Q72448985
• Mol file: 91419-52-2.mol

Synonyms:1-Boc-4-cyanopiperidine;91419-52-2;tert-butyl 4-cyanopiperidine-1-carboxylate;1-N-Boc-4-cyanopiperidine;n-boc-4-cyanopiperidine;1-n-boc-4-cyano-piperidine;N-Boc-4-cyano-piperidine;MFCD01861223;1-PIPERIDINECARBOXYLIC ACID, 4-CYANO-, 1,1-DIMETHYLETHYL ESTER;1-N-Boc-4-Cyano Piperidine;1-tert-butoxycarbonyl-4-cyanopiperidine;tert-butyl 4-cyano-1-piperidinecarboxylate;4-cyano-piperidine-1-carboxylic acid tert-butyl ester;1,1-DIMETHYLETHYL 4-CYANO-1-PIPERIDINECARBOXYLATE;4-CYANO-1-PIPERIDINECARBOXYLIC ACID 1,1-DIMETHYLETHYL ESTER;N-Boc 4-cyanopiperidine;4-cyano-1-boc piperidine;1-BOC-4-cyano-piperidine;BOC-4-CYANOPIPERIDINE;SCHEMBL311155;1-Boc-4-piperidinecarbonitrile;n-boc-piperidine-4-carbonitrile;DTXSID10363890;BCP22787;CS-D0644;4-cyano-1-t-butoxycarbonylpiperidine;AKOS005137876;AC-1039;AS-5646;BCP9000046;N-Boc-piperidine-4-carbonitrile, 97%;PB12957;1-(t-Butoxycarbonyl)-4-cyanopiperidine;1-tert-butyloxycarbonyl-4-cyanopiperidine;SY002521;AM20120319;B3962;FT-0601671;1-tert-Butoxycarbonyl-4-piperidinecarbonitrile;EN300-40306;B66757;4-Cyanopiperidine-1-carboxylic acid t-butyl ester;A904685;4-cyanopiperidin-1-carboxylic acid tert-butyl ester;J-524698;4-Cyano-1-piperidinecarboxylic Acid tert-Butyl Ester;1-(TERT-BUTOXYCARBONYL)PIPERIDINE-4-CARBONITRILE;F1915-8765;Z409418784;4-CYANOPIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

Chemical Property of 1-Boc-4-cyanopiperidine

Chemical Property:

• Appearance/Colour: yellowish oil
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 60-62 °C
• Refractive Index: 1.488
• Boiling Point: 325.3 °C at 760 mmHg
• PKA: -3.08±0.40(Predicted)
• Flash Point: 150.5 °C
• PSA: 53.33000
• Density: 1.07 g/cm³
• LogP: 2.09498
• Storage Temp.: 2-8°C
• Solubility.: Chloroform
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 210.136827821
• Heavy Atom Count: 15
• Complexity: 277

Purity/Quality:

1-tert-Butoxycarbonyl-4-cyanopiperidine >97.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 20/21/22:
• Hazard Codes: Xn,N
• Statements: 20/21/22-50-36-22
• Safety Statements: 36-36/37/39-61-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC(CC1)C#N
• Uses: Reactant for synthesis of:Aminomethylated fluoropiperidinesProtein kinase B inhibitorsGlyT1 inhibitorsPiperidinecarboxylic acids via nitrilase-catalyzed enantioselective synthesisReactant forReplacement in CB2 receptor inhibitorsDouble addition reactions of methyllithium and n-butyllithium to unsaturated nitriles

Technology Process of 1-Boc-4-cyanopiperidine

There total 29 articles about 1-Boc-4-cyanopiperidine 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: 100.0%

4-cyanopiperidine (4395-98-6) + di-tert-butyl dicarbonate (24424-99-5) → 1-tert-butoxycarbonyl-4-cyanopiperidine (91419-52-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 12h; Inert atmosphere;

Reference yield: 99.0%

tert-butyl 4-((hydroxyimino)methyl)piperidine-1-carboxylate (190446-85-6) → 1-tert-butoxycarbonyl-4-cyanopiperidine (91419-52-2)

Guidance literature:

With triethylamine; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In ethyl acetate; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1055/s-0034-1378881

Reference yield: 98.0%

4-carbamoyl-piperidine-1-carboxylic acid tert-butyl ester (91419-48-6) → 1-tert-butoxycarbonyl-4-cyanopiperidine (91419-52-2)

Guidance literature:

With triethylamine; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In ethyl acetate; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1055/s-0034-1378881

upstream raw materials:

4-cyanopiperidine

2,2-dimethylpropanoic anhydride

4-carbamoyl-piperidine-1-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

4-cyanopiperidine

tert-butyl 4-(1-amino-1-methylethyl)piperidine-1-carboxylate

4-(1H-tetrazol-5-yl)piperidine hydrochloride

4-(N-hydroxycarbamimidoyl)piperidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Xu, Jianyu,Twitty, J. Cameron,Watson, Mary P.. "Nickel-Catalyzed Deaminative Cyanation: Nitriles and One-Carbon Homologation from Alkyl Amines". supporting information. p. 6242 - 6245. Retrieved 2021/08/23.
• 2、 Gunaratna, Medha J.,Hua, Duy H.,Zou, Bende,Pascual, Conrado,Cao, William,Zhang, Man,Weerasekara, Sahani,Nguyen, Thi D.T.,Xiao, Kui,Xie, Xinmin Simon. "Synthesis of 1,4- and 1,4,4-substituted piperidines for the inhibition of neuronal T-type Ca2+ channels and mitigation of neuropathic pain in mice". . p. 22 - 39. Retrieved 2019/03/08.