3627-45-0

Basic information

• Product Name: 4-PHENYL-4-PIPERIDINE CARBOXYLIC ACID
• Synonyms: 4-phenyl-4-piperidinecarboxylicaci;4-phenyl-isonipecoticaci;4-phenylpiperidine-4-carboxylicacid;n-demthylmeperidinicacid;normeperidinicacid;4-PHENYL-4-PIPERIDINE CARBOXYLIC ACID;4-Phenyl-4-piperidinecarboxylic acid HCl;Norpethidinic acid
• CAS NO: 3627-45-0
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.25
• EINECS: 222-844-0
• Product Categories: pharmacetical
• Mol File: 3627-45-0.mol

Chemical Properties

• Boiling Point: 374.9 °C at 760 mmHg
• Flash Point: 180.5 °C
• Appearance: /
• Density: 1.157 g/cm³
• Vapor Pressure: 2.75E-06mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: 4-PHENYL-4-PIPERIDINE CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PHENYL-4-PIPERIDINE CARBOXYLIC ACID(3627-45-0)
• EPA Substance Registry System: 4-PHENYL-4-PIPERIDINE CARBOXYLIC ACID(3627-45-0)

Safety Data

• Hazardous Substances Data: 3627-45-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Phenyl-4-piperidine carboxylic acid is used as a key intermediate in the synthesis of CB1 antagonists with lowered propensity to pass the blood-brain-barrier. These antagonists are used in the treatment of various disorders, including obesity, metabolic syndrome, and drug addiction.
4-Phenyl-4-piperidine carboxylic acid is also used as a starting material in the synthesis of 4,4-disubstituted piperidines, which are NK1 antagonists. NK1 antagonists are used in the treatment of various conditions, including anxiety, depression, and pain.

InChI:InChI=1/C12H15NO2/c14-11(15)12(6-8-13-9-7-12)10-4-2-1-3-5-10/h1-5,13H,6-9H2,(H,14,15)

Upstream product

• 28233-54-7 1-cyano-4-phenyl-piperidine-4-carboxylic acid ethyl ester 
• 54824-07-6 methyl 4-phenylpiperidine-4-carboxylate 
• 101-41-7 benzeneacetic acid methyl ester 
• 61886-17-7 1-benzyl-4-phenyl-piperidine-4-carboxylic acid 
• 167262-68-2 N-(t-butyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acid 
• 51304-58-6 4-cyano-4-phenylpiperidine hydrochloride 
• 140-29-4 phenylacetonitrile 
• 37586-22-4 4-benzoylpiperidine 
• 96067-93-5 benzyl 4-(hydroxydiphenylmethyl)-piperidine-1-carboxylate 
• 916976-41-5 4-benzoyl-4-phenyl-piperidine-1-carboxylic acid benzyl ester 
• 916976-36-8 4-benzhydrylidene-piperidine-1-carboxylic acid benzyl ester 
• 922504-27-6 4-benzoylpiperidine-1-carboxylic acid benzyl ester 
• 181641-61-2 1-((benzyloxy)carbonyl)-4-phenylpiperidine-4-carboxylic acid 
• 57-42-1 pethidine 

Downstream Products

• 158144-85-5 1-t-butoxycarbonyl-4-phenyl-4-hydroxymethyl piperidine 
• 4220-08-0 (4-phenyl-piperidin-4-yl)-methanol 
• 160376-91-0 1-tert-butoxycarbonyl-4-phenyl-4[[(3,5-bis-trifluoromethyl)]benzyloxymethyl]piperidine 
• 1027259-36-4 4-Benzyloxymethyl-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester 
• 1026630-76-1 4-(3,5-Dimethyl-benzyloxymethyl)-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester 
• 1026458-87-6 4-(3,5-Dichloro-benzyloxymethyl)-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Achiral Derivatives of Hydroxamate AR-42 Potently Inhibit Class i HDAC Enzymes and Cancer Cell Proliferation

AR-42 is an orally active inhibitor of histone deacetylases (HDACs) in clinical trials for multiple myeloma, leukemia, and lymphoma. It has few hydrogen bond donors and acceptors but is a chiral 2-arylbutyrate and potentially prone to racemization. We report achiral AR-42 analogues incorporating a cycloalkyl group linked via a quaternary carbon atom, with up to 40-fold increased potency against human class I HDACs (e.g., JT86, IC50 0.7 nM, HDAC1), 25-fold increased cytotoxicity against five human cancer cell lines, and up to 70-fold less toxicity in normal human cells. JT86 was ninefold more potent than racAR-42 in promoting accumulation of acetylated histone H4 in MM96L melanoma cells. Molecular modeling and structure-activity relationships support binding to HDAC1 with tetrahydropyran acting as a hydrophobic shield from water at the enzyme surface. Such potent inhibitors of class I HDACs may show benefits in diseases (cancers, parasitic infections, inflammatory conditions) where AR-42 is active.

Design and synthesis of a new class of malonyl-CoA decarboxylase inhibitors with anti-obesity and anti-diabetic activities

A new series of thiazole-substituted 1,1,1,3,3,3-hexafluoro-2-propanols were prepared and evaluated as malonyl-CoA decarboxylase (MCD) inhibitors. Key analogs caused dose-dependent decreases in food intake and body weight in obese mice. Acute treatment with these compounds also led to a drop in elevated blood glucose in a murine model of type II diabetes.

LIMK2 INHIBITORS, COMPOSITIONS COMPRISING THEM, AND METHODS OF THEIR USE

Inhibitors of LIM kinase 2 are disclosed, along with pharmaceutical compositions comprising them and methods of their use. Particular compounds are of the formula:

CAN-mediated rearrangement of 4-benzhydrylidenepiperidines

Several 1-substituted phenyl-(4-phenylpiperidin-4-yl)methanones are synthesized in modest overall yields starting from the reaction of different 1-substituted 4-benzhydrylidenepiperidines via CAN-mediated rearrangement. This facile strategy was also used to synthesize meperidine analog.

Cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds

The present invention relates to novel cinnamide compounds that are useful for treating inflammatory and immunune diseases, to pharmaceutical compositions containing these compounds, and to methods of inhibiting inflammation or suppressing immune response in a mammal.

Cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds

The present invention relates to novel cinnamide compounds that are useful for treating inflammatory and immune diseases and cerebral vasospasm, to pharmaceutical compositions containing these compounds, and to methods of inhibiting inflammation or suppressing immune response in a mammal.

TLC identification adn GLC determination of meperidine and its metabolites in biological fluids.

Procedures were developed for TLC identification and GLC determination of meperidine and its metabolites, i.e., p-hydroxymeperidine, normeperidine, and meperidinic and normeperidinic acids. Meperidine, p-hydroxymeperidine, and normeperidine were extracted with ether from biological fluids at pH 10, whereas meperidinic and normeperidinic acids and conjugated metabolites remained in the aqueous phase. The residue, upon evaporation of the extract to dryness, was derivatized with trifluoroacetic anhydride and gas chromatographed. Total (free and conjugated) meperidinic and normeperidinic acids in the aqueous phase were converted and determined as meperidine and normeperidine, respectively. A preliminary result of urinary disposition of meperidine and its metabolites in the rat is presented. The identity of these metabolites was confirmed with GLC-mass spectrometry.