91419-52-2

Basic information

• Product Name: 1-Boc-4-cyanopiperidine
• Synonyms: 1-Piperidinecarboxylic acid, 4-cyano-, 1,1-dimethylethyl ester;Boc-4-cyanopiperidine;1-BOC-PIPERIDINE-4-CARBONITRILE;N-Boc-piperidine-4-carbonitrile;N-boc-4-cyanopiperidie;1-N-Boc-4-cyano-piperidine ,98%;1-Boc-4-cyanopiperid;N-tert-Butoxycarbonyl-4-cyanopiperidine
• CAS NO: 91419-52-2
• Molecular Formula: C₁₁H₁₈N₂O₂
• Molecular Weight: 210.27
• Product Categories: Boron, Nitrile, Thio,& TM-Cpds;Heterocycles;pharmacetical;Pyrans, Piperidines &Piperazines;Piperidine;Piperazine;Aromatics;Pyrans, Piperidines & Piperazines;Heterocyclic Building Blocks
• Mol File: 91419-52-2.mol

Chemical Properties

• Melting Point: 60-62°C
• Boiling Point: 325.3 °C at 760 mmHg
• Flash Point: 150.5 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.07 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: 2-8°C
• Solubility: Chloroform
• PKA: -3.08±0.40(Predicted)
• CAS DataBase Reference: 1-Boc-4-cyanopiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Boc-4-cyanopiperidine(91419-52-2)
• EPA Substance Registry System: 1-Boc-4-cyanopiperidine(91419-52-2)

Safety Data

• Hazard Codes: Xn,N
• Statements: 20/21/22-50-36-22
• Safety Statements: 36-36/37/39-61-26
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 91419-52-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Boc-4-cyanopiperidine is used as a reactant for the synthesis of Aminomethylated fluoropiperidines, which are important for the development of protein kinase B inhibitors. These inhibitors play a crucial role in regulating cellular processes and have potential applications in the treatment of various diseases, including diabetes and cancer.
1-Boc-4-cyanopiperidine is also used as a reactant for the synthesis of GlyT1 inhibitors. GlyT1 inhibitors are compounds that block the reuptake of glycine in the brain, which can be beneficial in the treatment of neurological disorders such as schizophrenia and depression.
Additionally, 1-Boc-4-cyanopiperidine is used as a reactant for the synthesis of piperidinecarboxylic acids via nitrilase-catalyzed enantioselective synthesis. These enantioselective methods allow for the production of chiral compounds with high purity, which is essential for the development of effective and safe pharmaceuticals.
Used in Agrochemical Industry:
1-Boc-4-cyanopiperidine is used as a reactant for the replacement in CB2 receptor inhibitors. CB2 receptor inhibitors have potential applications in the development of agrochemicals, as they can modulate the endocannabinoid system in plants, leading to improved growth, stress resistance, and crop yield.
1-Boc-4-cyanopiperidine is also used as a reactant in double addition reactions of methyllithium and n-butyllithium to unsaturated nitriles. These reactions are important in the synthesis of complex organic molecules, which can be used in the development of new agrochemicals and other industrial applications.

InChI:InChI=1/C11H18N2O2/c1-11(2,3)15-10(14)13-6-4-9(8-12)5-7-13/h9H,4-7H2,1-3H3

Upstream product

• 4395-98-6 4-cyanopiperidine 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 39546-32-2 4-carboxamidopiperidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 91419-48-6 4-carbamoyl-piperidine-1-carboxylic acid tert-butyl ester 
• 240401-22-3 piperidine-4-carbonitrile hydrochloride 
• 201230-82-2 carbon monoxide 
• 75-65-0 tert-butyl alcohol 
• 557-21-1 zinc(II) cyanide 
• 141699-59-4 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate 
• 22821-76-7 4-(methylsulfonyl)benzonitrile 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 5382-16-1 4-HYDROXYPIPERIDINE 
• 498-94-2 isonipecotic acid 

Downstream Products

• 912768-78-6 tert-butyl 4-(4-methylbenzoyl)piperidine-1-carboxylate 
• 280110-63-6 (Z)-tert-butyl 4-(N’-hydroxycarbamimidoyl)piperidine-1-carboxylate 
• 895132-38-4 tert-butyl 4-cyano-4-(pyridine-2-ylmethyl)piperidine-1-carboxylate 
• 1146664-36-9 C₁₇H₂₈N₂O₃ 
• 167262-98-8 tert-butyl 4-cyano-4-(pyridin-3-yl)piperidine-1-carboxylate 
• 167262-92-2 1-tert-butoxycarbonyl-4-cyano-4-(pyridin-4-yl)-piperidine 
• 1001467-84-0 C₁₆H₂₂N₄O₂S 
• 614730-96-0 tert-butyl 4-cyano-4-(hydroxymethyl) piperidine-1-carboxylate 
• 1416984-76-3 tert-butyl 4-(aminomethyl)-4-(hydroxymethyl)piperidine-1-carboxylate 
• 1338251-96-9 C₂₃H₂₆Cl₂N₂O₄ 
• 1338251-95-8 C₂₃H₂₆Cl₂N₂O₄ 
• 1338251-94-7 C₂₃H₂₆Cl₂N₂O₄ 
• 1338251-93-6 C₂₅H₃₂N₂O₅ 
• 1338251-92-5 C₂₉H₃₆N₂O₆ 

Relevant articles and documents

Sustainable Route Toward N-Boc Amines: AuCl3/CuI-Catalyzed N-tert-butyloxycarbonylation of Amines at Room Temperature

N-tert-butoxycarbonyl (N-Boc) amines are useful intermediates in synthetic/medicinal chemistry. Traditionally, they are prepared via an indirect phosgene route with poor atom economy. Herein, a step- and atom-economic synthesis of N-Boc amines from amines, t-butanol, and CO was reported at room temperature. Notably, this N-tert-butyloxycarbonylation procedure utilized ready-made substrates, commercially available AuCl3/CuI as catalysts, and O2 from air as the sole oxidant. This catalytic system provided unique selectivity for N-Boc amines in good yields. More significantly, gram-scale preparation of medicinally important N-Boc amine intermediates was successfully implement, which demonstrated a potential application prospect in industrial syntheses. Furthermore, this approach also showed good compatibility with tertiary and other useful alcohols. Investigations of the mechanisms revealed that gold catalyzed the reaction and copper acted as electron transfer mediator in the catalytic cycle.

Nickel-Catalyzed Deaminative Cyanation: Nitriles and One-Carbon Homologation from Alkyl Amines

A nickel-catalyzed deaminative cyanation of Katritzky pyridinium salts has been developed. When it is coupled with formation of the pyridinium salt from primary amines, this method enables alkyl amines to be converted to alkyl nitriles. A less toxic cyanide reagent, Zn(CN)2, is utilized, and diverse functional groups and heterocycles are tolerated. The method also enables a one-carbon homologation of alkyl amines via reduction of the nitrile products, in addition to many other potential transformations of the versatile nitrile group.

Nickel-Catalyzed Cyanation of Unactivated Alkyl Sulfonates with Zn(CN)2

Cyanation of unactivated primary and secondary alkyl mesylates with Zn(CN)2 catalyzed by nickel has been developed. The reaction provides an efficient route for the synthesis of alkyl nitriles with wide substrate scope, good functional group tolerance, and compatibility with heterocyclic compounds. Mechanistic studies indicate that alkyl iodide generated in situ serves as the reactive intermediate and the gradual release of alkyl iodide is crucial for the success of the reaction.

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

A dysregulation in function of neuronal low-voltage-activated T-channel causes neuropathic pain. A group of ten 1,4-disubstituted and 1,4,4-trisubstituted piperidines were synthesized through short sequences of reactions from 4-cyanopiperidine, which may potentially produce a library of analogs. Inhibitions of T-channel in rat dorsal root ganglion neurons and/or Cav3.2 channel in human embryonic kidney-293 cells were screened, and subsequent analgesic effects and inhibition of seizure in pentylenetetrazole-induced seizure mouse model were examined. The two most promising piperidine molecules showed analgesic effects in rat model using a spared nerve injury protocol. One displayed a long withdrawal latency in response to thermal stimulation, and an 80% increase in mechanical threshold assessment studies.

Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis

An operationally simple method is disclosed for the decarboxylative cyanation of aliphatic carboxylic acids at room temperature. Riboflavin tetraacetate, which is an inexpensive organic photocatalyst, promotes the oxidation of carboxylic acids upon visible-light activation. After decarboxylation, the generated radicals are trapped by TsCN, yielding the desired nitriles without any further additive, in a redox-neutral process. Importantly, this protocol can be adapted to flow conditions.

ION CHANNEL INHIBITORY COMPOUNDS, PHARMACEUTICAL FORMULATIONS AND USES

The present invention is directed towards new chemical entities which primarily inhibit the human T-type calcium channels and differentially modulate other key ion channels to control cell excitability, and abnormal neuronal activity particularly involved in the development and maintenance of persistent or chronic pain, and / or neurological disorders. These novel compounds are useful in the treatment and prevention of neurological and psychiatric disorders and diseases in which these ion channels are involved. The invention is also directed towards pharmaceutical formulations comprising these compounds and the uses of these compounds.

A practical iodine-catalyzed oxidative conversion of aldehydes to nitriles

A simple and efficient method for the direct synthesis of nitriles from aldehydes using ammonium acetate as the nitrogen source has been developed. The reactions were performed with iodine as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant under mild conditions. A variety of aromatic, heteroaromatic, aliphatic and allylic aldehydes could be converted into their corresponding nitriles in good to excellent yields.

Discovery of Potent, Selective, and Orally Bioavailable Small-Molecule Modulators of the Mediator Complex-Associated Kinases CDK8 and CDK19

The Mediator complex-associated cyclin-dependent kinase CDK8 has been implicated in human disease, particularly in colorectal cancer where it has been reported as a putative oncogene. Here we report the discovery of 109 (CCT251921), a potent, selective, and orally bioavailable inhibitor of CDK8 with equipotent affinity for CDK19. We describe a structure-based design approach leading to the discovery of a 3,4,5-trisubstituted-2-aminopyridine series and present the application of physicochemical property analyses to successfully reduce in vivo metabolic clearance, minimize transporter-mediated biliary elimination while maintaining acceptable aqueous solubility. Compound 109 affords the optimal compromise of in vitro biochemical, pharmacokinetic, and physicochemical properties and is suitable for progression to animal models of cancer.

INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL

The present invention provides compounds of Formula I and the pharmaceutically acceptable salts thereof, which are inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention.

Deboronative cyanation of potassium alkyltrifluoroborates: Via photoredox catalysis

A photoredox catalytic method was developed for the direct cyanation of alkyltrifluoroborates. This reaction provides a new and useful transformation of the easily available alkyltrifluoroborates. The photocatalytic reaction can tolerate a variety of functional groups with mild reaction conditions. Mechanistic investigations are consistent with the present reaction following a radical pathway.