85098-64-2

Basic information

• Product Name: 4-Anilino-1-benzyl-4-piperidinecarboxylic acid
• Synonyms: 1-benzyl-4-(phenylamino)piperidine-4-carboxylic acid;4-(Phenylamino]-1-benzyl-4-piperidinecarboxylic Acid;4-Anilino-1-benzylpiperidine-4-carboxylic Acid;NSC 73748;4-Piperidinecarboxylicacid,4-(phenylamino)-1-(phenylmethyl)-;1-BENZYL-4-PHENYLAMINO-4-CARBOXY-PIPERIDINE;1-Benzyl-4-anilinopiperidine-4-carboxylic acid;4-(Phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylic acid
• CAS NO: 85098-64-2
• Molecular Formula: C₁₉H₂₂N₂O₂
• Molecular Weight: 310.39018
• EINECS: 285-415-7
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 85098-64-2.mol

Chemical Properties

• Boiling Point: 495.6 °C at 760 mmHg
• Flash Point: 253.5 °C
• Appearance: Grey Solid
• Density: 1.234 g/cm³
• Vapor Pressure: 1.22E-10mmHg at 25°C
• Refractive Index: 1.643
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly)
• CAS DataBase Reference: 4-Anilino-1-benzyl-4-piperidinecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Anilino-1-benzyl-4-piperidinecarboxylic acid(85098-64-2)
• EPA Substance Registry System: 4-Anilino-1-benzyl-4-piperidinecarboxylic acid(85098-64-2)

Safety Data

• Hazardous Substances Data: 85098-64-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Anilino-1-benzyl-4-piperidinecarboxylic acid is used as a potential analgesic agent for its ability to provide pain relief. Its chemical structure and properties make it a promising candidate for the development of new medications aimed at treating various types of pain.

InChI:InChI=1/C19H22N2O2/c22-18(23)19(20-17-9-5-2-6-10-17)11-13-21(14-12-19)15-16-7-3-1-4-8-16/h1-10,20H,11-15H2,(H,22,23)

Upstream product

• 1096-03-3 1-benzyl-4-phenylaminopiperidine-4-carboxylic acid amide 
• 3612-20-2 1-phenylmethyl-4-piperidone 
• 968-86-5 1-benzyl-4-(phenylamino)piperidine-4-carbonitrile 
• 62-53-3 aniline 
• 67-66-3 chloroform 

Downstream Products

• 63260-82-2 ethyl 1-benzyl-4-phenylamino-4-piperidinecarboxylate 
• 61086-04-2 4-(N-phenylamino)-1-phenylmethyl-4-piperidinylmethanol 
• 256507-84-3 1-benzyl-4-[phenyl(propionyl)amino]piperidine-4-carboxylic acid 
• 61085-60-7 methyl 4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylate 
• 61085-72-1 methyl 4-[N-(1-oxopropyl)-N-phenylamino]-1-benzyl-4-piperidinecarboxylate 
• 72996-78-2 methyl 4-[N-(1-oxopropyl)-N-phenylamino]-4-piperidinecarboxylate 
• 1217504-89-6 C₁₉H₂₂⁽²⁾H₂N₂O 
• 61380-02-7 4-(methoxymethyl)-N-phenyl-1-(phenylmethyl)-4-piperidinamine 

Relevant articles and documents

SUBSTITUTED N-(2-(AMINO)-2-OXOETHYL)BENZAMIDE INHIBITORS OF AUTOTAXIN AND THEIR PREPARATION AND USE IN THE TREATMENT OF LPA-DEPENDENT OR LPA-MEDIATED DISEASES

The present invention relates to compounds according to Formula I and pharmaceutically acceptable salts, synthesis, intermediates, formulations, and methods of disease treatment therewith, including cancer, lymphocyte homing, chronic inflammation, neuropathic pain, fibrotic diseases, thrombosis, and cholestatic pruritus, mediated at least in part by ATX.

A facile method for preparation of [2H3]-sufentanil and its metabolites

An improved process for the synthesis of sufentanil with an overall yield of 26% is described. The reactive and high yielding N-debenzylation of the piperidine intermediate 7 using a mixture of Pd/C and Pd(OH)2 was applied to other drug intermediates affording free amines in short reaction times. The deuterium-labeled sufentanil and the metabolite desmethylsufentanil were synthesized applying the optimized process.

Aromatic amines as nucleophiles in the Bargellini reaction

Aromatic amines can be employed in the Bargellini reaction to generate useful intermediates. Rapid, practical access to functionalised, privileged structures may have significant utility in the synthesis of drug-like molecules. An improved synthesis of carfentanil analogues illustrates this point.

MUSCARINIC MODULATORS

The present invention relates to modulators of muscarinic receptors. The present invention also provides compositions comprising such modulators, and methods therewith for treating muscarinic receptor mediated diseases.

Syntheses, biological evaluation, and molecular modeling of 18F-labeled 4-anilidopiperidines as μ-opioid receptor imaging agents

The synthesis, evaluation, and molecular modeling of a series of 18F-labeled 4-anilidopiperidines with high affinities for the μ-opioid receptor (μ-OR) are reported. On the basis of the high brain uptake and selective retention in brain regions that contain a high concentration of the μ-OR, combined with a good metabolic stability, [ 18F]fluoro-pentyl carfentanil ([18F]4) and 2-(±)[18F]-fluoropropyl-sufentanil ([18F]6) were selected as the lead compounds for further evaluation. The binding affinity to the human μ-OR was 0.74 and 0.13 nM for [18F]4 and [ 18F]6, respectively. In vitro autoradiography of [18F] 4 and [18F] 6 on rat brain sections produced patterns in accordance with the known distribution of μ-OR expression. Structure-activity relationships of the fluorinated compounds are discussed with respect to the interaction with an activated-state model of the μ-OR. Taken together, the in vivo and in vitro data indicate that [18F] 4 and [18F] 6 hold promise for studying the μ-opioid receptor in humans by means of positron emission tomography.

SYNTHESIS OF PIPERIDINE DERIVATIVES AS POTENTIAL ANALGETIC AGENTS

Reaction of N-(1-(2-phenylethyl)-4-piperidinyl)propionanilide (I) with phosphorus pentasulfide gave the thioamide VI.Acylation of N-(1-(2-phenylethyl)-4-piperidinyl)aniline with 2-(methoxy)acetic and 2-(methylthio)acetic anhydrides afforded the amides II and III.Treatment of 4-anilino-1-benzylpiperidine-4-methanol with thionyl chloride gave the spirocyclic sulfurous acid ester amide XIV.Reduction of the hydrochloride of ethyl 3-(1-ethoxycarbonyl-4-phenylimino-3-piperidinyl)propionate (XXII) with sodium cyanoborohydride gave the perhydro-1,6-naphthyridine derivative XIX, a model compound in the synthesis of the cyclic analogue of fentanyl (I).Ethyl 4-anilino-1-(2-phenylethyl)-1,2,3,6-tetrahydropyridine-3-carboxylate (XXIX) hydrochloride, obtained by reaction of ethyl 4-oxo-1-(2-phenylethyl)piperidine-3-carboxylate hydrochloride with aniline, was reduced with lithium aluminium hydride to 4-anilino-1-(2-phenylethyl)piperidine-3-methanol (XXXI). 1-Methyl- and 1-benzyl-4-piperidone were reacted with 4-cyclopropylphenylmagnesium bromide and the tertiary alcohols XXXVII and XXXVIII obtained were acylated with propionyl chloride to give the esters XXXIX and XL.The piperidine derivatives XLI, XLVI and XLVIII were prepared as potential neurotropic agents.Alkylation of 8-hydroxy-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine (XLIX) with 2-(2-chloroethyl)-1,3-dioxane and -1,3-dioxolane resulted in the 6,7-benzomorphan derivatives L and LI.Out of the compounds prepared, only the closest fentanyl analogues II, III, and VI showed very strong analgetic activity.

Synthesis and pharmacological evaluation of 4,4-disubstituted piperidines

A new class of piperidine derivatives is added to the increasing family of compounds related to fentanyl and carfentanil. Herein, we describe the synthesis and pharmacology of a number of 1-(arylethyl)-4-(acylamino)-4-[(acyloxy)-methyl]piperidines such as 9, 15, and 23. As expected, many of these congeners of fentanyl are extremely potent narcotic agonists. The aim of the study was to identify short-acting analgesic agents (i.e. less than 6 min in the mouse hot-plate assay) for possible use in the surgical theater. Many of the drugs proved to be of intermediate and long duration (i.e. 6-15 min and > 15 min, respectively). In addition to analgesic activity, many of the compounds exhibited anesthetic properties as well. The structure-activity relationship for these entities is presented and discussed.

N-Aryl-N-(1-L-4-piperidinyl)-arylacetamides

Novel N-aryl-N-(1-L-4-piperidinyl)arylacetamides useful as anti-arrhythmic agents, a method of treating arrhythmia which comprises the systemic administration of such compounds to warm-blooded animals and pharmaceutical compositions to be used therefor.

N-aryl-N-(1-alkyl-4-piperidinyl)-arylacetamides

Novel N-aryl-N-(1-L-4-piperidinyl)arylacetamides useful as antiarrhythmic agents, a method of treating arrhythmia which comprises the systemic administration of such compounds to warm-blooded animals and pharmaceutical compositions to be used therefor.