1155-56-2

Basic information

• Product Name: 4-ANILINO-1-BENZYLPIPERIDINE
• Synonyms: N-(1-Benzyl-4-piperidinyl)benzenamine;N-Phenyl-1-(phenylmethyl)-4-piperidinamine;4-Piperidinamine, N-phenyl-1-(phenylmethyl)-;Fentanyl Related Compound D (10 mg) (N-Phenyl-1-(phenylmethyl)-4-piperidinamine);1-Benzyl-4-(phenylaMino)piperidine;1-Benzyl-4-anilinopiperidine;NSC 76613;Fentanyl Related CoMpound D
• CAS NO: 1155-56-2
• Molecular Formula: C18H22N2
• Molecular Weight: 266.38
• EINECS: 214-583-6
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1155-56-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 848-886 °C
• Boiling Point: 404.619 °C at 760 mmHg
• Flash Point: 158.462 °C
• Appearance: /
• Density: 1.106 g/cm³
• Vapor Pressure: 9.32E-07mmHg at 25°C
• Storage Temp.: Refrigerator
• Solubility: Soluble in dichloromethane.
• PKA: 8.18±0.10(Predicted)
• CAS DataBase Reference: 4-ANILINO-1-BENZYLPIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ANILINO-1-BENZYLPIPERIDINE(1155-56-2)
• EPA Substance Registry System: 4-ANILINO-1-BENZYLPIPERIDINE(1155-56-2)

Safety Data

• Hazardous Substances Data: 1155-56-2(Hazardous Substances Data)

Usage

Description

4-Anilino-1-benzylpiperidine is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceuticals. It is an orange liquid with unique chemical properties that make it valuable in the development of different medications.

Uses

Used in Pharmaceutical Industry:
4-Anilino-1-benzylpiperidine is used as a pharmaceutical intermediate for the development of various medications. Its unique chemical structure allows it to be a key component in the synthesis of a wide range of drugs.
Used in the Preparation of Fentanyl Derivatives:
In the field of anesthetic and pain management, 4-anilino-1-benzylpiperidine is utilized as an intermediate in the preparation of fentanyl derivatives. Fentanyl is a potent synthetic opioid used for severe pain management, and its derivatives are crucial in developing more effective and safer analgesics.
Chemical Properties:
4-Anilino-1-benzylpiperidine is characterized by its orange liquid appearance, which is indicative of its unique chemical properties. These properties make it a valuable compound in the pharmaceutical industry for the development of new and improved medications.

InChI:InChI=1/C18H22N2/c1-3-7-16(8-4-1)15-20-13-11-18(12-14-20)19-17-9-5-2-6-10-17/h1-10,18-19H,11-15H2/p+1

Upstream product

• 41979-39-9 4-piperidone hydrochloride 
• 100-39-0 benzyl bromide 
• 62-53-3 aniline 
• 100-46-9 benzylamine 
• 793-19-1 bis(2-methoxycarbonylethyl)benzylamine 
• 3612-20-2 1-phenylmethyl-4-piperidone 
• 1155-57-3 N-(1-benzylpiperidin-4-ylidene)aniline 

Downstream Products

• 864738-99-8 4-[N-(aminocarbonyl)phenylamino]-1-phenylmethylpiperidine 
• 473871-16-8 1,2,3,4-tetrahydro-1-[1-[4-(1-methylethyl)-cyclohexyl]-4-piperidinyl]-quinolin-2-one 
• 1437759-78-8 C₂₂H₂₆N₂O 
• 149054-20-6 1-(1-benzyl-piperidin-4-yl)-3,4-dihydro-1H-quinolin-2-one 
• 1437759-66-4 C₂₁H₂₅ClN₂O 
• 1437759-76-6 C₂₂H₂₇ClN₂O 
• 1437759-84-6 C₂₂H₂₇ClN₂O 
• 1616854-83-1 1-(1-benzylpiperidin-4-yl)indoline-2,3-dione 
• 1605-98-7 N-[1-(2-oxo-2-phenyl-ethyl)-piperidin-4-yl]-N-phenyl-butyramide 

Relevant articles and documents

Novel quinolone-based potent and selective HDAC6 inhibitors: Synthesis, molecular modeling studies and biological investigation

In this work we describe the synthesis of potent and selective quinolone-based histone deacetylase 6 (HDAC6) inhibitors. The quinolone moiety has been exploited as an innovative bioactive cap-group for HDAC6 inhibition; its synthesis was achieved by applying a multicomponent reaction. The optimization of potency and selectivity of these products was performed by employing computational studies which led to the discovery of the diethylaminomethyl derivatives 7g and 7k as the most promising hit molecules. These compounds were investigated in cellular studies to evaluate their anticancer effect against colon (HCT-116) and histiocytic lymphoma (U9347) cancer cells, showing good to excellent potency, leading to tumor cell death by apoptosis induction. The small molecules 7a, 7g and 7k were able to strongly inhibit the cytoplasmic and slightly the nuclear HDAC enzymes, increasing the acetylation of tubulin and of the lysine 9 and 14 of histone 3, respectively. Compound 7g was also able to increase Hsp90 acetylation levels in HCT-116 cells, thus further supporting its HDAC6 inhibitory profile. Cytotoxicity and mutagenicity assays of these molecules showed a safe profile; moreover, the HPLC analysis of compound 7k revealed good solubility and stability profile.

Synthesis and Biological Evaluation of Fentanyl Analogues Modified at Phenyl Groups with Alkyls

A series of fentanyl analogues modified at the phenyl group of the phenethyl with alkyl and/or hydroxyl and alkoxy, and the phenyl group in the anilido moiety replaced with benzyl or substituted benzyl, were synthesized. The in vitro opioid receptor functional activity of these compounds was evaluated by assessment of their ability to modulate forskolin-stimulated cAMP accumulation and by their ability to induce β-arrestin2 recruitment. Compound 12 is a potent μ-opioid (MOP) receptor agonist, a potent κ-opioid (KOP) receptor antagonist with weak β-arrestin2 recruitment activity. Compounds 10 and 11 are potent MOP receptor agonists with weak δ-opioid (DOP) receptor antagonist activity and moderate KOP receptor antagonist activity as well as weak β-arrestin2 recruitment activity at the MOP receptor. These compounds are promising leads for discovery of potent opioid analgesics with reduced side effects relative to clinically available strong opioid analgesics.

An Operationally Simple Synthesis of Fentanyl Citrate

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