27969-75-1

Basic information

• Product Name: 3-Piperidin-1-ylaniline
• Synonyms: 3-(1-Piperidino)aniline;1-(3-Aminophenyl)piperidine;AKOS BB-8948;3-PIPERIDIN-1-YLANILINE;3-Piperidin-1-ylaniline 95%;3-(PIPERIDIN-1-YL)PHENYLAMINE;BenzenaMine,3-(1-piperidinyl)-;3-(1-piperidinyl)Benzenamine
• CAS NO: 27969-75-1
• Molecular Formula: C₁₁H₁₆N₂
• Molecular Weight: 176.26
• Mol File: 27969-75-1.mol

Chemical Properties

• Boiling Point: 346.7 °C at 760 mmHg
• Flash Point: 141.1 °C
• Appearance: /
• Density: 1.074 g/cm³
• Vapor Pressure: 5.64E-05mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: 3-Piperidin-1-ylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Piperidin-1-ylaniline(27969-75-1)
• EPA Substance Registry System: 3-Piperidin-1-ylaniline(27969-75-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 23-26-36/37/39
• Hazardous Substances Data: 27969-75-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Piperidin-1-ylaniline is used as a key intermediate in the synthesis of antipsychotic drugs such as brexpiprazole and cariprazine. It contributes to the development of medications that address various psychiatric conditions by modulating specific neurotransmitter pathways in the brain.
Used in Organic Chemistry:
In the realm of organic chemistry, 3-Piperidin-1-ylaniline serves as a catalyst to facilitate chemical reactions, enhancing the efficiency and selectivity of synthetic processes. Its unique structure makes it a valuable component in the design of new catalysts.
Used in Research for Neurological Disorders:
3-Piperidin-1-ylaniline is utilized in scientific research as a potential therapeutic agent for neurological disorders. Its exploration in this field is driven by the need for new treatments that can address the complex nature of these conditions.
Used in Dyes and Pigments Production:
3-Piperidin-1-ylaniline is also used as an intermediate in the production of dyes and pigments, where its chemical properties contribute to the color and stability of these products in various applications, including textiles, plastics, and printing inks.

InChI:InChI=1/C11H16N2/c12-10-5-4-6-11(9-10)13-7-2-1-3-8-13/h4-6,9H,1-3,7-8,12H2

Upstream product

• 110-89-4 piperidine 
• 108-37-2 1-bromo-3-chlorobenzene 
• 626-01-7 3-Iodoaniline 
• 402-67-5 3-fluoro-1-nitrobenzene 
• 27969-73-9 1‐(3‐nitrophenyl)piperidine 

Downstream Products

• 922524-44-5 N-[3-(piperidin-1-yl)phenyl]-D,L-leucine 
• 27292-50-8 3-piperidinophenol 
• 1152500-40-7 C₁₅H₂₂N₂ 
• 1062073-37-3 C₂₅H₂₄ClN₃O 

Relevant articles and documents

1,3-Aza-Brook Rearrangement of Aniline Derivatives: In Situ Generation of 3-Aminoaryne via 1,3-C-(sp2)-to-N Silyl Migration

The design, synthesis, and validation of 3-aminobenzyne precursors induced by C-(sp2)-to-N 1,3-aza-Brook rearrangement have been achieved, allowing access to diverse aniline derivatives. Through crossover experiments, we demonstrated the intramolecular mechanism of 1,3-C-to-N silyl transfer. To gain insight into the regioselectivity observed in the reactions, we performed density functional theory calculations. Finally, the method was applied to the synthesis of xylanigripones A in five linear steps in an overall yield of 30%.

Inter-alkane amidogen phenolic synthetic method (by machine translation)

Inter-alkane amidogen phenolic synthetic method, its characteristic is: 1st step, between the two alkane amidogen acyl aniline and sulfuric acid aqueous solution mixing and heating to 50 - 110 °C, thermal insulation reaction of aniline [...] sulfuric acid aqueous solution; 2nd step, continue to drip the sodium nitrite aqueous solution, sodium nitrite aqueous solution for dropping temperature of - 10 - 20 °C, drop bi yu 5 - 30 °C insulation, [...] aniline obtained diazonium salt of the sulfuric acid aqueous solution; 3rd step, [...] aniline diazonium salt of the sulfuric acid aqueous solution is directly heated to 45 - 110 °C, thermal insulation, in the hydrolysis reaction of the diazonium salt, cooling after treatment, to obtain the product between two alkane amidogen phenol; three-step required by the reaction of sulfuric acid in the 1st step reaction in the finished disposable adding; a three-step reaction in a finish step by step in the pot. The method of the invention with raw materials are cheap, abundant, synthetic high security of the process, the product yield is high, the three waste less pollution and the like, has high industrial value. (by machine translation)

DIARYLUREAS AS CB1 ALLOSTERIC MODULATORS

The present invention provides novel diarylurea derivatives (compounds of formula (I)) and their uses. The compounds of the present invention are demonstrated to be allosteric modulators of the CB1 receptor, and therefore useful for the treatment of diseases and conditions mediated by CB1.

Catalyst-Directed Chemoselective Double Amination of Bromo-chloro(hetero)arenes: A Synthetic Route toward Advanced Amino-aniline Intermediates

A chemoselective sequential one-pot coupling protocol was developed for preparing several amino-anilines in high yield as building blocks for active pharmaceutical ingredients (APIs). Site (Cl vs Br on electrophile) and nucleophile (amine vs imine) selectivity is dictated by the catalyst employed. A Pd-crotyl(t-BuXPhos) precatalyst selectively coupled the Ar-Br of the polyhaloarene with benzophenone imine, even in the presence of a secondary amine, while Pd-based RuPhos or (BINAP)Pd(allyl)Cl coupled the Ar-Cl site with secondary amines.

Design and synthesis of potent dual inhibitors of JAK2 and HDAC based on fusing the pharmacophores of XL019 and vorinostat

Specifically blocking more than one oncogenic pathway simultaneously in a cancer cell with a combination of different drugs is the mainstay of the majority of cancer treatments. Being able to do this via two targeted pathways without inducing side effects through a general mechanism, such as chemotherapy, could bring benefit to patients. In this work we describe a new dual inhibitor of the JAK-STAT and HDAC pathways through designing and developing two types of molecule based on the JAK2 selective inhibitor XL019 and the pan-HDAC inhibitor, vorinostat. Both series of compounds had examples with low nanomolar JAK2 and HDAC1/6 inhibition. In some cases good HDAC1 selectivity was achieved while retaining HDAC6 activity. The observed potency is explained through molecular docking studies of all three enzymes. One example, 69c had 16–25 fold selectivity against the three other JAK-family proteins JAK1, JAK3 and TYK2. A number of compounds had sub-micromolar potencies against a panel of 4 solid tumor cell lines and 4 hematological cell lines with the most potent compound, 45h, having a cellular IC50 of 70 nM against the multiple myeloma cell line KMS-12-BM. Evidence of both JAK and HDAC pathway inhibition is presented in Hela cells showing that both pathways are modulated. Evidence of apoptosis with two compounds in 4 sold tumor cell lines is also presented.

A fragment merging approach towards the development of small molecule inhibitors of Mycobacterium tuberculosis EthR for use as ethionamide boosters

With the ever-increasing instances of resistance to frontline TB drugs there is the need to develop novel strategies to fight the worldwide TB epidemic. Boosting the effect of the existing second-line antibiotic ethionamide by inhibiting the mycobacterial

Direct hydrogenation of nitroaromatics and one-pot amidation with carboxylic acids over platinum nanowires

A novel ultrathin platinum nanowire with uniform length and a diameter of 1.5 nm was synthesized by acidic etching of FePt nanowire in methanol. This nanowire was characterized by high-resolution transmission electron microscopy (HRTEM). X-ray diffraction (XRD) data indicated that the main plane is (111). The ability of this nanowire to catalyze the heterogeneous hydrogenation of nitroaromatics to give the corresponding amines has been investigated. The catalyst showed satisfactory activity in various solvents under mild conditions and showed excellent stability. The catalytic performance was also evaluated in the one-pot reduction of nitroaromatics and amidation with carboxylic acids under a hydrogen atmosphere at 100°C. These methods for the hydrogenation of nitroaromatics and the direct amidation of nitroaromatics with carboxylic acids are simple, economical, and environmentally benign, and have practical advantages for the synthesis of amines and amides without the production of toxic byproducts.

Catalytic asymmetric intramolecular hydroarylations of ω-aryloxy- and arylamino-tethered α,β-unsaturated aldehydes

The first enantioselective organocatalytic intramolecular hydroarylations of phenol and aniline-derived enals were investigated. The proposed method provided an atom economic and straightforward approach to optically active chromans and tetrahydroquinolines in high enantioselectivities and in good yields. The study demonstrated the efficiency of organocatalysis to achieve the first asymmetric intramolecular arylation of ω aryloxy- arylamino-tethered α, and β-unsaturated aldehydes using a chiral secondary amine catalyst. Proposed transformation method resulted in the production of functionalized chromans and tetrahydroquinoline in high enantiopurity. The study also examined the scope of substrates in this organocatalytic reaction using a catalyst 4/p-TsOH.H2O in diethyl ether. The catalyst screening observed a higher yield up to 83% and comparable enantiometric excess up to 88% that can be obtained in a chiral secondary amine employed as the reaction catalyst.

Antiprion activity of functionalized 9-aminoacridines related to quinacrine

A library of functionalized 6-chloro-2-methoxy-(N9-substituted)acridin-9-amines structurally related to quinacrine were synthesized and evaluated for antiprion activity on four different cell models persistently infected with scrapie prion strains (ScN2a, N167, Ch2) or a human disease prion strain (F3). Most of the compounds were distinguished by the side chain attached to 9-amino of the acridine ring. These were dialkylaminoalkyl and phenyl with basic groups on the phenyl ring. The most promising compound was 6-chloro-2-methoxy-N-(4-(4-methylpiperazin-1-yl)phenyl)acridin-9-amine (15) which had submicromolar EC50 values (0.1-0.7 μM) on all cell models, was able to clear PrPSc at non-toxic concentrations of 1.2-2.5 μM, and was more active than quinacrine in terms of EC50 values. Other promising compounds were 14 (a regioisomer of 15) and 17 which had a 1-benzylpiperidin-4-yl substituent attached to the 9-amino function. Activity was strongly dependent on the presence of a substituted acridine ring, which in this library comprised 6-chloro-2-methoxy substituents on the acridine ring. The side chains of 14, 15, and 17 have not been previously associated with antiprion activity and are interesting leads for further optimization of antiprion activity.

Potent and selective cathepsin K inhibitors

A novel series of cathepsin K inhibitors derived from Novartis compound I is described. Optimization of the P1, P3, and P1′ units led to the identification of 4-aminophenoxyacetic acid 24b with an IC50 value of 4.8 nM, which possessed an excell