1530-87-6

Usage

Chemical Properties

CLEAR ALMOST COLOURLESS LIQUID

Uses

1-Piperidinecarbonitrile was used in the preparation of 1-selenocarbamoylpiperidine.

General Description

1-Piperidinecarbonitrile in tetrahydrofuran (THF) reacts with a solution of piperidyl lithium in THF at 0°C to yield lithium[1,1,3,3-bis(pentamethylene)guanidinate]. It participates in thermal decomposition of the 2H-azaphosphirene metal complexes to yield the Δ3-1,3,2-oxazaphospholene complexes and the Δ3-1,3,2-thiazaphospholene complexes.

InChI:InChI=1/C6H10N2/c7-6-8-4-2-1-3-5-8/h1-5H2

Upstream product

• 626-67-5 N-methylcyclohexylamine 
• 506-68-3 bromocyane 
• 880-09-1 di(N-piperidinyl)methane 
• 3010-03-5 piperidin-1-yl-acetonitrile 
• 110-89-4 piperidine 
• 70989-48-9 2-thioxo-benzooxazole-3-carboximidic acid p-tolyl ester 
• 656835-57-3 C-benzotriazol-1-yl-C-piperidin-1-yl-methyleneamine 
• 151-50-8 potassium cyanide 
• 5211-86-9 N-(dimethoxymethyl)piperidine 
• 14446-67-4 N-allylpiperidine 
• 61929-24-6 2-bromo-1,3,4-thiadiazole 
• 7677-24-9 trimethylsilyl cyanide 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 
• 1622-87-3 2-(piperidin-1-yl)acetamide 

Downstream Products

• 5606-32-6 6-piperidino-[1,3,5]-triazine-2,4-diamine 
• 128118-65-0 6-Chloro-5-phenyl-2-piperidin-1-yl-[1,3]oxazin-4-one 
• 104132-45-8 N-(Phenylglyoxyloyl)-1-piperidincarboximidoylchlorid 
• 76098-52-7 N-(3,4-Dioxo-2-phenyl-cyclobut-1-enyl)-piperidine-1-carboximidoyl bromide 
• 90697-67-9 6-Phenyl-2-piperidino-4,4-bis(trifluormethyl)-4H-1,3,5-oxadiazin 
• 76098-40-3 C₁₃H₁₄Cl₂N₂OS 
• 130564-80-6 Piperidine-1-carbothioic acid [3,4-diphenyl-[1,3]thiazetidin-(2E)-ylidene]-amide 
• 76098-33-4 N-[1-Chloro-1-piperidin-1-yl-meth-(E)-ylidene]-4-nitro-benzamide 
• 104132-63-0 (E)-N-(2-Oxo-4-phenyl-3-butenoyl)-1-piperidincarboximidoylchlorid 
• 114943-64-5 2-(1-Phenylethylideneamino)-4,6-bis(1-piperidino)-1,3,5-oxadiazinium hexachloroantimonate 
• 104132-57-2 N-(4-Bromphenylglyoxyloyl)-1-piperidincarboximidoylchlorid 
• 76098-37-8 (E)-N-[1-Chloro-1-piperidin-1-yl-meth-(E)-ylidene]-3-(4-nitro-phenyl)-acrylamide 
• 2158-03-4 1-piperidinecarboxamide 
• 29044-24-4 N-(N-hydroxyamidino)piperidine 

Relevant academic research and scientific papers

Peracid oxidation of an N-hydroxyguanidine compound: A chemical model for the oxidation of N(ω)-hydroxy-L-arginine by nitric oxide synthase

Arginine is oxidized by a class of enzymes called the nitric oxide synthases (NOS) to generate citrulline and, presumably, nitric oxide (·NO). N-Hydroxylation of a guanidinium nitrogen of arginine to generate N- hydroxyarginine (NOHA) has been shown to be a step in the biosynthesis of ·NO. In an effort to elucidate the mechanism by which further oxidation of NOHA occurs, the oxidation of a model N-hydroxyguanidine compound by several peracids was studied in depth. This oxidative chemistry is a possible model for the enzymatic process since the corresponding urea (or citrulline equivalent product) is obtained along with an oxidized nitrogen species. The oxidized nitrogen product was, however, not ·NO but rather HNO. ·NO generation in this chemical system and in the enzymatic process would require another one-electron oxidation. The mechanistic details of this are further discussed.

Electrochemical strategies for: N -cyanation of secondary amines and α C -cyanation of tertiary amines under transition metal-free conditions

Transition metal-free electrochemical approaches for the N-cyanation of secondary amines and the α C-cyanation of tertiary amines have been well established, with products being obtained in moderate to good yields and with good functional group tolerance under ambient conditions. The synthetic application of the protocols has been highlighted through scale-up experiments in a galvanostatic mode. Preliminary mechanistic investigation has confirmed that TBAB played a critical role in N-cyanation transformation and has indicated that the transformation might proceed via a free radical process. This journal is

N-Cyanation of Primary and Secondary Amines with Cyanobenzio-doxolone (CBX) Reagent

An efficient electrophilic N-cyanation of amines with a stable and less-toxic cyanobenziodoxole reagent towards the synthesis of cyanamides is disclosed. This synthetically practicable strategy allows the construction of a wide variety of cyanamides under very mild and simple conditions with a broad functional group compatibility, and showcases a huge potential in late-stage modification of complex molecules.

Preparation method of cyano tertiary amine

The invention relates to the technical field of organic synthesis methods, in particular to a preparation method of N, N-disubstituted cyanamide. According to the invention, secondary amine and 2-bromo-1, 3, 4-thiadiazole, 2, 5-dibromo-1, 3, 4-thiadiazole or 2-bromo-5-methyl-1, 3, 4-thiadiazole are used as raw materials to prepare N, N-disubstituted cyano tertiary amine under the catalysis of a metal salt; the synthetic process is simple, the yield is high, the toxicity of the raw materials is extremely low, the reaction temperature is low, the reaction time is sort, the aftertreatment is simple, and the preparation process is a green preparation process with universality. The method for preparing N, N-disubstituted cyanamide solves the problems of low yield, high toxicity of raw materials, no universality, difficulty in asymmetric disubstituted synthesis and the like in the existing preparation process, and has industrial large-scale application prospects.

Tris(3,5-dimethylpyrazolyl)methane copper(I) complexes featuring one disubstituted cyanamide ligand

The complexes [Cu{HC(3,5-Me2pz)3}(NCNR2)][BF4] (1–8; R2 = Me2 1, Et2 2, C5H10 3, C4H8O 4, C4H8 5, C3H

A allyl uncle amine compound by one-step synthesis method of cyano uncle amine compound (by machine translation)

The invention relates to a one-step synthesis of amine compound allyl unclecyano uncle amine compounds, which belongs to the technical field of organic synthetic method. The method specific synthetic process is as follows: in the airtight reaction environment, to the anhydrous organic solvent is added in the cyanogen bromide, under protection of inert gas, and then added dropwise to the solution in the allylic and high yield amine compound, to obtain allyl uncle amine compound concentration is 0.8 - 1 mol/L solution, at room temperature the reaction 16 - 24 hours later, after column chromatography separation and purification, to obtain a corresponding cyano uncle amine compound. The method to get rid of the expensive deallylation use of the catalyst, the synthesis step is less, raw materials are easy, cheap, mild reaction conditions, the operation is simple, easy to craft and industrialization. Yield 50% - 80% between. (by machine translation)

Synthesis of Cyanamides from Cyanogen Bromide under Mild Conditions through N-Cyanation of Allylic Tertiary Amines

Cyanamides were selectively formed through a one-step nucleophilic substitution reaction of allylic tertiary amines with cyanogen bromide. Because of the mild reaction conditions and good yields of the reaction, as well as the commercial availability of the starting materials, this new method represents a valuable tool for the synthesis of cyan-amides through an N-deallylation reaction and an N-cyanation reaction in one pot.

A copper-mediated oxidative N-cyanation reaction

Copper-promoted N-cyanation of aliphatic sec-amine by CuCN is achieved via oxidative coupling. This procedure employs O2 as a clean oxidant. Notably, sulfoximines and 1,1,3,3-tetramethylguanidine also worked well in this procedure. Thus, it represents a key progress in the C-N bond formation reaction as well as in the cyanation reaction. This journal is the Partner Organisations 2014.

Iron(III) catalysed synthesis of unsymmetrical di and trisubstituted ureas - A variation of classical Ritter reaction

An application of the classical Ritter reaction for the synthesis of unsymmetrical di and trisubstituted ureas catalyzed by FeCl3 is described. The protocol is of significant interest in view of the easy availability of precursors, mild reaction conditions employed and interestingly its applicability for the alkylation of alcohols capable of forming stable carbocationic intermediates even to the sterically hindered moieties. The Royal Society of Chemistry 2012.

HETEROCYCLIC DERIVATIVE HAVING INHIBITORY ACTIVITY ON TYPE-I 11 -HYDROXYSTEROID DEHYDROGENASE

Disclosed is a compound which is useful as an 11β-hydroxysteroid dehydrogenase type 1 inhibitor. A compound represented by the formula: its pharmaceutically acceptable salt, or a solvate thereof, wherein X is O or S, a broken line and a wavy line represent the presence or the absence of a bond, (i) when a broken line represents the presence of a bond, a wavy line represents the absence of a bond, R2 and R3 are each independently hydrogen, halogen, cyano, hydroxy, carboxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like, (ii) when a broken line represents the absence of a bond, a wavy line represents the presence of a bond, R1 and R4 are each independently hydrogen, halogen or the like, R2 and R3 are each independently hydrogen, halogen, cyano, hydroxy, carboxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like, and R5 and R6 are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like.