72752-52-4

Basic information

• Product Name: 2-PIPERIDINOBENZONITRILE
• Synonyms: 2-PIPERIDINOBENZENECARBONITRILE;2-PIPERIDINOBENZONITRILE;2-(1-PIPERIDINO)BENZONITRILE;BUTTPARK 33\12-73;1-(2-cyanophenyl)piperidine;2-(1-PIPERIDINE)BENZONITRILE;2-(1-Piperidinyl)benzonitrile, 97%;Piperidinyl)benzonitril
• CAS NO: 72752-52-4
• Molecular Formula: C₁₂H₁₄N₂
• Molecular Weight: 186.25
• EINECS: 427-380-4
• Mol File: 72752-52-4.mol

Chemical Properties

• Melting Point: 45 °C
• Boiling Point: 122-125°C 1mm
• Flash Point: 122-125°C/1mm
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 0.000108mmHg at 25°C
• Refractive Index: 1.577
• Storage Temp.: 2-8°C
• PKA: 3.61±0.40(Predicted)
• BRN: 1243909
• CAS DataBase Reference: 2-PIPERIDINOBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PIPERIDINOBENZONITRILE(72752-52-4)
• EPA Substance Registry System: 2-PIPERIDINOBENZONITRILE(72752-52-4)

Safety Data

• Statements: 20/21/22
• Safety Statements: 22-36/37/39
• RIDADR: 3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 72752-52-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-PIPERIDINOBENZONITRILE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds, contributing to the development of new medications.
Used in Organic Synthesis:
It is utilized as a building block in the production of a range of organic substances, expanding its applications beyond the pharmaceutical sector.
Used in Central Nervous System Drug Production:
2-PIPERIDINOBENZONITRILE is used as a key component in the creation of drug molecules that target the central nervous system, such as antipsychotic drugs, due to its structural and functional properties.
Used in Research and Development:
2-PIPERIDINOBENZONITRILE is employed in studies investigating its potential biological activities and pharmacological properties, which may lead to the discovery of new therapeutic applications.

InChI:InChI=1/C12H14N2/c13-10-11-6-2-3-7-12(11)14-8-4-1-5-9-14/h2-3,6-7H,1,4-5,8-9H2

Upstream product

• 201230-82-2 carbon monoxide 
• 157428-86-9 N-(but-3-enyl)-2-cyanobenzenamine 
• 110-89-4 piperidine 
• 873-32-5 2-Chlorobenzonitrile 
• 394-47-8 2-fluorobenzonitrile 
• 611-20-1 salicylonitrile 
• 138313-23-2 2-<(trifluoromethanesulfonyl)oxy>benzonitrile 

Downstream Products

• 131269-45-9 (Z)-2-Piperidino-benzamidoxim 
• 147769-96-8 3-methyl-1-[2-(piperidin-1-yl)phenyl]butan-1-imine 
• 72752-54-6 (2-(piperidin-1-yl)phenyl)methanamine 
• 34595-26-1 2-(piperidin-1-yl)benzaldehyde 
• 332347-70-3 3-methyl-1-(2-(1-piperidinyl)phenyl)butan-1-ol 
• 42093-97-0 2-(piperidin-1-yl)benzoic acid 
• 1417704-54-1 N-[1-(2-piperidino-phenyl)vinyl]acetamide 
• 1620165-39-0 (Z)-N-(1-(2-(piperidin-1-yl)phenyl)-4-(triisopropylsilyl)but-1-en-3-yn-1-yl)acetamide 
• 219922-18-6 ethyl 2-ethoxy-4-<2-<<1-<2-(1-piperidinyl)phenyl>ethyl>amino>-2-oxoethyl>-benzoate 
• 219922-80-2 4-<3-<2-(1-piperidinyl)phenyl>-2,2-ethylenedioxy-heptyl>-benzoic acid 
• 219921-27-4 2-hydroxy-4-[N-{1-(2-piperidino-phenyl)-1-butyl}-aminocarbonylmethyl]-benzoic acid 
• 219922-32-4 (S)-(-)-ethyl 4-<2-<methyl>amino>-2-oxoethyl>-benzoate 
• 219922-31-3 (R)-(+)-ethyl 4-<2-<methyl>amino>-2-oxoethyl>-benzoate 
• 83901-40-0 (-)-AZ-DF 265 

Relevant articles and documents

SNAr reaction in aqueous medium in the presence of mixed organic and inorganic bases

N-Arylation of amines with fluorobenzonitriles in aqueous medium is described. A mixture of N,N-diisopropylethyl amine and Na2CO3 (1:1) is found to achieve maximum conversion by refluxing for 3 hours in water. The product can be easily isolated by solvent extraction.

Rhodium(iii)-catalyzed olefinic C-H alkynylation of enamides at room temperature

Rh(iii)-catalyzed C-H olefinic alkynylation of enamides for the stereospecific construction of synthetically useful Z-type enynamides is reported. This protocol displays good functionality tolerance and operational simplicity thus providing an alternative synthetic opportunity for the ease of access to specific 1,3-enyne derivatives.

Efficient construction of C=N double bonds via acceptorless dehydrogenative coupling

The efficient construction of C=N double bonds has been achieved by the Ir-catalyzed intramolecular acceptorless dehydrogenative cross-coupling of tertiary amines and amides. An iridium/2-hydroxypyridine complex was identified as the highly efficient catalyst. A number of quinazolinone derivatives was prepared in excellent yields. An iridium-mediated C-H activation mechanism is proposed. This finding provides an unprecedented strategy for the direct imidation of sp3 C-H bonds.

Design and synthesis of 6-fluoro-2-naphthyl derivatives as novel CCR3 antagonists with reduced CYP2D6 inhibition

In our previous study on discovering novel types of CCR3 antagonists, we found a fluoronaphthalene derivative (1) that exhibited potent CCR3 inhibitory activity with an IC50 value of 20 nM. However, compound 1 also inhibited human cytochrome P450 2D6 (CYP2D6) with an IC50 value of 400 nM. In order to reduce its CYP2D6 inhibitory activity, we performed further systematic structural modifications on 1. In particular, we focused on reducing the number of lipophilic moieties in the biphenyl part of 1, using C log D7.4 values as the reference index of lipophilicity. This research led to the identification of N-{(3-exo)-8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]oct-3-yl}-3-(piperidin-1-ylcarbonyl)isonicotinamide 1-oxide (30) which showed comparable CCR3 inhibitory activity (IC50 = 23 nM) with much reduced CYP2D6 inhibitory activity (IC50 = 29,000 nM) compared with 1.

Substituted compounds derived from N-(benzyl)phenylacetamide, preparation and uses

This invention relates to poly-substituted derivatives of the N-(benzyl)phenylacetamide type, pharmaceutical compositions comprising same, therapeutic uses thereof, more particularly in the fields of human and animal health. This invention also relates to a process for the preparation of such derivatives.

An improved process for repaglinide via an efficient and one pot process of (1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butan-1-amine - A useful intermediate

The development of a large-scale synthesis for (1S)-3-methyl-1-(2- piperidin-1-ylphenyl)butan-1-amine (S-(+)-1), a key intermediate of repaglinide (2), is described. The process conditions for S-(+)-1 involving nucleophilic substitution, Grignard reaction, reduction and resolution were optimized and telescoped. The racemization of the undesired enantiomer R-(-)-1 offers a distinctive advantage in terms of cost and overall yield over the existing process. This communication also describes the control of a DCU byproduct obtained during the condensation of S-(+)-1 with phenyl acetic acid derivative 3 in the synthesis of 2. Schweizerische Chemische Gesellschaft.

Method of inhibiting neoplastic cells with imidazoquinazoline derivatives

A method for inhibiting neoplasia, particularly cancerous and precancerous lesions by exposing the affected cells to imidazoquinazoline derivatives.

Imidazoquinazoline derivatives

PCT No. PCT/JP97/03023 Sec. 371 Date Apr. 27, 1998 Sec. 102(e) Date Apr. 27, 1998 PCT Filed Aug. 29, 1997 PCT Pub. No. WO98/08848 PCT Pub. Date Mar. 5, 1998Imidazoquinoline derivatives of the formula (wherein X may be O or S) provide selective cyclic guanosine 3',5' monophosphate (cGMP)-specific phosphodiesterase (PDE) inhibitory activity. The compounds are useful for treating or ameliorating cardiovascular disease such as thrombosis, angina pectoris, hypertension, heart failure and arterial sclerosis, as well as asthma, impotence and the like.

A facile route to aryl amines: Nucleophilic substitution of aryl triflates

The aromatic nucleophilic substitution (S(N)Ar) between aryl triflates and secondary amines has been studied. In the absence of solvent, the reaction proceeds at room temperature for nitro and cyano activated aryl triflates and requires higher temperatures in the case of carboxy activation. Variable triflate reactivity could be explained in terms of frontier molecular orbital theory. This methodology has been applied for the synthesis of substituted piperidyl pyridines.

Repaglinide and related hypoglycemic benzoic acid derivatives

The structure-activity relationships in two series of hypoglycemic benzoic acid derivatives (5, 6) were investigated. Series 5 resulted from meglitinide (3) when the 2-methoxy was replaced by an alkyleneimino residue. Maximum activity was observed with the cis-3,5-dimethylpiperidino (5h) and the octamethyleneimino (5l) residues. Series 6 resulted from the meglitinide analogon 4 bearing an inversed amido function when the 2-methoxy, the 5- fluoro, and the α-methyl residue were replaced by a 2-piperidino, a 5- hydrogen, and a larger α-alkyl residue, respectively. An alkoxy residue ortho to the carboxy group further increased activity and duration of action in the rat. The most active racemic compound, 6al (R4 = isobutyl; R = ethoxy), turned out to be 12 times more active than the sulfonylurea (SU) glibenclamide (1). Activity was found to reside predominantly in the (S)- enantiomers. Compared with the SUs 1 and 2 (glimepiride), the most active enantiomer, (S)-6al (AG-EE 623 ZW; repaglinide; ED50 = 10 μg/kg po), is 25 and 18 times more active. Repaglinide turned out to be a useful therapeutic for type 2 diabetic patients; approval was granted recently by the FDA and the EMEA. From investigations on the pharmacophoric groups in compounds of type 5 and 6, it was concluded that in addition to the two already known - the acidic group (COOH; S02NH) and the amidic spacer (CONH; NHCO) - the ortho residue R1 (alkyleneimino; alkoxy; oxo) must be regarded as a third one. A general pharmacophore model suitable for hypoglycemic benzoic acid derivatives, SUs, and sulfonamides is proposed (Figure 6). Furthermore, from superpositions of low-energy conformations (LECs) of 1, 2, and (S)-6al, it was concluded that a common binding conformation (LEC II; Figure 10B) may exist and that differences in binding to the SU receptor and in the mechanism of insulin release between repaglinide and the two SUs may be due to specific hydrophobic differences.