1-N-Boc-3-cyanopiperidine

Base Information

• Chemical Name: 1-N-Boc-3-cyanopiperidine
• CAS No.: 91419-53-3
• Molecular Formula: C₁₁H₁₈N₂O₂
• Molecular Weight: 210.276
• Hs Code.: 29335990
• European Community (EC) Number: 672-488-9
• DSSTox Substance ID: DTXSID10373535
• Nikkaji Number: J828.297H
• Mol file: 91419-53-3.mol

Synonyms:91419-53-3;1-N-Boc-3-cyanopiperidine;n-boc-3-cyanopiperidine;tert-butyl 3-cyanopiperidine-1-carboxylate;1-Boc-3-cyanopiperidine;(+/-)-1-n-boc-3-cyano-piperidine;MFCD01861222;(s)-1-boc-3-cyanopiperidine;1-Piperidinecarboxylic acid, 3-cyano-, 1,1-dimethylethyl ester;(r)-1-boc-3-cyanopiperidine;3-cyano-1-piperidinecarboxylic acid tert-butyl ester;N-Boc-3-cyano-piperidine;1-n-boc-3-cyano-piperidine;(R)-1-N-Boc-3-cyano-piperidine;MFCD05864632;3-cyano-piperidine-1-carboxylic acid tert-butyl ester;1-tert-Butoxycarbonyl-3-cyanopiperidine;8-Naphthol-1-carboxylic acid;1-Boc-3-piperidinecarbonitrile;SCHEMBL1970337;DTXSID10373535;UEFZTXGFHKPSFS-UHFFFAOYSA-N;CS-D0645;AKOS005146015;AB22692;AB22871;AC-2374;PB12772;1-BOC-PIPERIDINE-3-CARBONITRILE;1-Boc-piperidine-3-carbonitrile, 95%;AM807444;AS-16165;SY004325;SY018027;tert-Butyl 3-Cyano-1-piperidinecarboxylate;B4515;FT-0601672;FT-0653753;FT-0659846;1-tert-Butoxycarbonyl-3-piperidinecarbonitrile;EN300-56899;B66755;1-(tert-Butoxycarbonyl)-3-piperidinecarbonitrile;A843862;A860466;Q-103082;F8889-6640;Z859818128;METHYL4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE

Chemical Property of 1-N-Boc-3-cyanopiperidine

Chemical Property:

• Vapor Pressure: 0.000232mmHg at 25°C
• Melting Point: 60-65℃
• Refractive Index: 1.487
• Boiling Point: 325.3 °C at 760 mmHg
• PKA: -3.42±0.40(Predicted)
• Flash Point: 150.5 °C
• PSA: 53.33000
• Density: 1.07 g/cm³
• LogP: 2.09498
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: soluble in Methanol
• 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: 285

Purity/Quality:

96% 1H NMR ^*data from raw suppliers

N-Boc-3-Cyanopiperidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-36/37/38-50
• Safety Statements: 26-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC(C1)C#N

Technology Process of 1-N-Boc-3-cyanopiperidine

There total 5 articles about 1-N-Boc-3-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%

tert-butyl 3-carbamoylpiperidine-1-carboxylate (91419-49-7) → (+/-)-2-N-tert-butoxycabonylpiperidine-3-carbonitrile (91419-53-3)

Guidance literature:

With pyridine; trichlorophosphate; at 0 - 20 ℃;

Reference yield:

N-(tert-butyloxycarbonyl)nipecotic acid (71381-75-4,88495-54-9,84358-12-3) → (+/-)-2-N-tert-butoxycabonylpiperidine-3-carbonitrile (91419-53-3)

Guidance literature:

Multi-step reaction with 2 steps

1: di-tert-butyl dicarbonate; NH₄HCO₃; pyridine / dioxane / 20 h / 20 °C

2: Et₃N; trifluoroacetic anhydride / CH₂Cl₂ / 3.5 h / 20 °C

With pyridine; di-tert-butyl dicarbonate; ammonium bicarbonate; triethylamine; trifluoroacetic anhydride; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jm070027u

Reference yield:

nipecotic acid (498-95-3,262853-93-0) → (+/-)-2-N-tert-butoxycabonylpiperidine-3-carbonitrile (91419-53-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide / tert-butyl alcohol / 12 h / 0 - 20 °C

2.1: triethylamine; isobutyl chloroformate / dichloromethane / 1 h / 0 - 20 °C

2.2: 0 °C

3.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 16 h / 20 °C

With triethylamine; trifluoroacetic anhydride; sodium hydroxide; isobutyl chloroformate; In dichloromethane; tert-butyl alcohol;

upstream raw materials:

tert-butyl 3-carbamoylpiperidine-1-carboxylate

N-(tert-butyloxycarbonyl)nipecotic acid

nipecotic acid

di-tert-butyl dicarbonate

Downstream raw materials:

5-<1-(tert-butoxycarbonyl)-3-piperidyl>-1H-tetrazole

tert-butyl 3-[amino(hydroxyimino)methyl]piperidine-1-carboxylate

tert-butyl 3-(4-{[(4-fluorobenzyl)amino]carbonyl}-5,6-dihydroxypyrimidin-2-yl)piperidine-1-carboxylate

tert-butyl 3-(aminomethyl)piperidine-1-carboxylate

Refernces

• 1、 -. "MK2 INHIBITORS AND USES THEREOF". Paragraph 00606. . Retrieved 2014/10/03.
• 2、 -. "Substituted Oxadiazole Derivatives as Positive Allosteric Modulators of Metabotropic Glutamate Receptors". Page/Page column 11. . Retrieved 2009/09/07.