176022-03-0

Basic information

• Product Name: 3S,4R-4-[phenyl-1-methylpiperidinyl] methanol
• Synonyms: 3S,4R-4-[phenyl-1-methylpiperidinyl] methanol;[(3S,4R)-4-Phenyl-1-methylpiperidinyl]methanol,99%e.e.;Paroxetine Impurity 7
• CAS NO: 176022-03-0
• Molecular Formula: C13H19NO
• Molecular Weight: 205.29606
• Mol File: 176022-03-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3S,4R-4-[phenyl-1-methylpiperidinyl] methanol(CAS DataBase Reference)
• NIST Chemistry Reference: 3S,4R-4-[phenyl-1-methylpiperidinyl] methanol(176022-03-0)
• EPA Substance Registry System: 3S,4R-4-[phenyl-1-methylpiperidinyl] methanol(176022-03-0)

Safety Data

• Hazardous Substances Data: 176022-03-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3S,4R-4-[phenyl-1-methylpiperidinyl] methanol is used as a chiral building block for the synthesis of various drugs and pharmaceutical compounds. Its unique stereochemistry allows for the production of enantiomerically pure compounds, which is essential for the development of effective and safe medications.
Used in Antipsychotic Drug Synthesis:
3S,4R-4-[phenyl-1-methylpiperidinyl] methanol is used as a key intermediate in the production of antipsychotic drugs. Its specific configuration contributes to the compound's ability to modulate neurotransmitter systems in the brain, helping to alleviate symptoms associated with psychotic disorders.
Used in Antiemetic Drug Development:
3S,4R-4-[phenyl-1-methylpiperidinyl] methanol is also utilized in the development of antiemetic drugs, which are medications designed to prevent or treat nausea and vomiting. Its chiral nature ensures that the synthesized drugs are effective in targeting the appropriate receptors in the body, minimizing side effects.
Used in Novel Pharmaceutical Agent Development:
3S,4R-4-[phenyl-1-methylpiperidinyl] methanol is employed in the research and development of new pharmaceutical agents for the treatment of various medical conditions. Its versatility as a chiral building block allows for the exploration of innovative drug candidates with potential therapeutic benefits.

Upstream product

• 116140-25-1 (+/-)-6-oxo-4t-phenyl-piperidine-3r-carboxylic acid ethyl ester 
• 86219-77-4 3-hydroxymethyl-1-methyl-4-phenyl-1,2,3,4-tetrahydropyridine 
• 626-67-5 N-methylcyclohexylamine 
• 263769-50-2 (+)-Methyl 4β-(4-Bromophenyl)-1-methylpiperidine-3β-carboxylate 
• 178634-04-3 (+)-trans-3-(4-hydroxyphenoxymethyl)-1-methyl-4-phenylpiperidine 
• 14371-10-9 (E)-3-phenylpropenal 

Relevant articles and documents

Transition-Metal-Free Multiple Functionalization of Piperidines to 4-Substituted and 3,4-Disubstituted 2-Piperidinones

Remote and multiple functionalization of piperidines without the use of transition-metal catalysts and elaborate directing groups is one of the major challenges in organic synthesis. Herein is reported an unprecedented two-step protocol that enables the multiple functionalization of piperidines to either 4-substituted or trans-3,4-disubstituted 2-piperidones. First, by exploiting the duality of TEMPO reactivity, which under oxidative and thermal conditions fluctuates between cationic and persistent-radical form, a novel multiple C(sp3)-H oxidation of piperidines to α,β-unsaturated 2-piperidones was developed. Second, the intrinsic low reactivity of the unsaturated piperidones toward conjugated Grignard additions was overcome by using trimethylsilyl chloride (TMSCl) as Lewis acid. Subsequently, conjugated Grignard addition/electrophilic trapping protocol provided substituted 2-piperidone intermediates, some of which were then transformed into pharmaceutical alkaloids.

Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands

Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18F-fluorination of aryl boron reagents with 18F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.

Highly enantioselective organocatalytic cascade reaction for the synthesis of piperidines and oxazolidines

The synthesis of piperidines and piperidines derivatives in enantiopure fashion has been a challenging goal for organic chemists. In this report we developed a nice cascade reaction for piperidine derivatives based in an amidomalonate Michael addition to enals followed by an intramolecular hemiaminal formation with good yields and enantioselectivities. Moreover we studied the 'in situ' intramolecular cyclization of this hemiaminals with alcohols forming fused piperidine-oxazolidines.

CYCLOALKANOPYRIDINE DERIVATIVE

Provided are cycloalkanopyridine derivatives of formula [I]: [wherein the symbols are the same as those stated in the description]. The compounds act as a nociceptin receptor antagonist, and are useful as medicines for diseases associated with a nociceptin receptor, for example, as a reliever against tolerance to a narcotic analgesic; a reliever against dependence on or addiction to a narcotic analgesic; an analgesic enhancer; an antiobesitic or appetite suppressor; a treating or prophylactic agent for cognitive impairment and dementia/amnesia; an agent for treating developmental cognitive abnormality; a remedy for schizophrenia; an agent for treating neurodegenerative diseases; an anti-depressant or treating agent for affective disorder; a treating or prophylactic agent for diabetes insipidus; a treating or prophylactic agent for polyuria; or a remedy for hypotension.

NOVEL PROCESS FOR THE PREPARATION OF 4-ARYL-3-HYDROXYMETHYL-1-METHYLPIPERIDINES.

A novel, improved, and general process for the preparation of 4-aryl-3-hydroxymethyl-1-methylpiperidines is disclosed in the present invention. 4-(4-Fluorophenyl)-3-hydroxymethyl-1-methylpiperidine is a well-known intermediate in making the anti-depressan

Monomeric and dimeric heterocycles, and therapeutic uses thereof

The invention provides compounds of formula (I):X—L—X1??(I)wherein X and X1 are substituted piperidine, cyclohexane, or tetrahydropyran rings, and L is a linking group between X and X1; as well a pharmaceutical composition comprising a compound of formula I; intermediates and methods useful for preparing a compound of formula I; and therapeutic methods for treating drug addiction, Parkinson's disease, depression, or a disease wherein the administration of cocaine is indicated, comprising administering a compound of formula I or a pharmaceutically acceptable salt thereof to a mammal in need of such treatment.

Process for the preparation of 3-substituted 4-phenyl-piperidine derivatives

Described herein is the process for the preparation of 3-substituted 4-phenyl-piperidine derivatives of formula (I) in which X is selected from H and F, and R is selected from the group consisting of H, C1-C6 alkyl, C3-C6 alkenyl, and benzyl, comprising three steps starting from the monoamide of malonic acid and cinnamic aldehyde, or derivatives thereof.

Synthesis and 5HT modulating activity of stereoisomers of 3-phenoxymethyl-4-phenylpiperidines

A series of pairs of enantiomers of substituted 3-phenoxymethyl-4-phenylpiperidines has been prepared from arecoline or α-methylstyrene by a combination of stereospecific reactions and optical resolutions. The ability of the compounds to modulate serotonin (5HT) neurotransmission in vitro was determined. Several derivatives, among which is the antidepressant paroxetine, are very potent inhibitors of 5HT reuptake. These compounds exhibit a pronounced steric requirement for inhibition of 5HT reuptake and binding to 5HT2A and 5HT2C receptors. Acta Chemica Scandinavica 1996.

ON THE FORMATION OF THE 1-AZA-(3.1.1)-BICYCLOHEPTANE RING SYSTEM

The preveously unpublished bicyclic system 1-aza-(3.1.1)-biycyloheptane has been shown to exist as an unexpected intermediate in the synthesis of Femoxetine, a CNS active drug.