177948-43-5

Basic information

• Product Name: 1-BOC-4-(4-FLUORO-BENZYLAMINO)-PIPERIDINE
• Synonyms: 1-BOC-4-(4-FLUORO-BENZYLAMINO)-PIPERIDINE;tert-butyl 4-((4-fluorophenyl)methyl)aminopiperidine carboxylate
• CAS NO: 177948-43-5
• Molecular Formula: C₁₇H₂₅FN₂O₂
• Molecular Weight: 308.39
• Mol File: 177948-43-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-BOC-4-(4-FLUORO-BENZYLAMINO)-PIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BOC-4-(4-FLUORO-BENZYLAMINO)-PIPERIDINE(177948-43-5)
• EPA Substance Registry System: 1-BOC-4-(4-FLUORO-BENZYLAMINO)-PIPERIDINE(177948-43-5)

Safety Data

• Hazardous Substances Data: 177948-43-5(Hazardous Substances Data)

Usage

Chemical compound

A substance formed by the chemical combination of two or more elements in a fixed proportion.

Used in synthesis

It is utilized in the creation of other compounds, particularly in the pharmaceutical and agrochemical industries.

Pharmaceutical applications

It has potential uses in the development of new drugs for treating various diseases.

Agrochemical applications

It is relevant in the agricultural industry for the production of pesticides and herbicides.

Piperidine derivative

It is a type of compound derived from piperidine, which is a heterocyclic amine.

BOC protecting group

The compound has a tert-butyloxycarbonyl (BOC) group, which serves as a temporary modification to protect the molecule during synthesis.

4-(4-Fluoro-benzylamino) substitution

The compound features a 4-(4-fluoro-benzylamino) group attached to the piperidine ring, which contributes to its unique properties and potential applications.

Medicinal chemistry relevance

Its structure and properties make it valuable in the field of medicinal chemistry, particularly for designing molecules with specific biological activities.

Building block

The unique structure of 1-BOC-4-(4-FLUORO-BENZYLAMINO)-PIPERIDINE allows it to be used as a building block for creating diverse molecules with targeted biological effects.

Upstream product

• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 140-75-0 para-fluorobenzylamine 
• 459-57-4 4-fluorobenzaldehyde 
• 87120-72-7 1-(tert-butoxycarbonyl)-4-aminopiperidine 

Downstream Products

• 1246458-44-5 tert-butyl 4-(3-(4-(benzyloxy)benzyl)-1-(4-fluorobenzyl)ureido)piperidine-1-carboxylate 
• 1246458-46-7 tert-butyl 4-(3-(4-benzyloxy-3-methoxybenzyl)-1-(4-fluorobenzyl)ureido)piperidine-1-carboxylate 
• 1246458-48-9 tert-butyl 4-(3-(3-benzyloxy-4-methoxybenzyl)-1-(4-fluorobenzyl)ureido)piperidine-1-carboxylate 
• 1091682-31-3 [1-((S)-2-amino-3,3-dimethyl-butyryl)-piperidin-4-yl]-(4-fluoro-benzyl)-carbamic acid benzyl ester hydrochloride 
• 1091682-30-2 (R)-2-cyclopentylmethyl-N-{(S)-1-[4-(4-fluoro-benzylamino)-piperidine-1-carbonyl]-2,2-dimethyl-propyl}-3-(formyl-hydroxy-amino)-propionamide 

Relevant articles and documents

11C-labeling and preliminary evaluation of pimavanserin as a 5-HT2A receptor PET-radioligand

Pimavanserin is a selective serotonin 2A receptor (5-HT2AR) inverse agonist that has shown promise for treatment of psychotic symptoms in patients with Parkinson's disease. Here, we detail the 11C-labeling and subsequently evaluate pimavanserin as a PET-radioligand in pigs. [11C]Pimavanserin was obtained by N-methylation of an appropriate precursor using [11C]MeOTf in acetone at 60 °C giving radiochemical yields in the range of 1-1.7 GBq (n = 4). In Danish Landrace pigs the radio ligand readily entered the brain and displayed binding in the cortex in accordance with the distribution of 5-HT2ARs. However, this binding could not be blocked by either ketanserin or pimavanserin itself, indicating high nonspecific binding. The lack of displacement by the 5-HT2R antagonist and binding in the thalamus suggests that [11C]pimavanserin is not selective for the 5-HT2AR in pigs.

Novel derivatives of urea and use thereof

The present invention relates to a novel urea derivative compound and 5HT thereof. 2A The present invention relates to the use of antagonists as antagonists for the prevention or treatment of neuropsychiatric disorders, degenerative brain diseases, propagated disorders and/or metabolic diseases.

Design, Synthesis, and Biological Evaluation of New Peripheral 5HT2A Antagonists for Nonalcoholic Fatty Liver Disease

Nonalcoholic fatty liver disease (NAFLD) is increasingly prevalent worldwide, causing serious liver complications, including nonalcoholic steatohepatitis. Recent findings suggest that peripheral serotonin (5-hydroxytryptamine, 5HT) regulates energy homeostasis, including hepatic lipid metabolism. More specifically, liver-specific 5HT2A knockout mice exhibit alleviated hepatic lipid accumulation and hepatic steatosis. Here, structural modifications of pimavanserin (CNS drug), a 5HT2A antagonist approved for Parkinson's disease, led us to synthesize new peripherally acting 5HT2A antagonists. Among the synthesized compounds, compound 14a showed good in vitro activity, good liver microsomal stability, 5HT subtype selectivity, and no significant inhibition of CYP and hERG. The in vitro and in vivo blood-brain barrier permeability study proved that 14a acts peripherally. Compound 14a decreased the liver weight and hepatic lipid accumulation in high-fat-diet-induced obesity mice. Our study suggests new therapeutic possibilities for peripheral 5HT2A antagonists in NAFLD.

Identification of novel aminopiperidine derivatives for antibacterial activity against Gram-positive bacteria

We have previously reported amidopiperidine derivatives as a novel peptide deformylase (PDF) inhibitor and evaluated its antibacterial activity against Gram-positive bacteria, but poor pharmacokinetic profiles have resulted in low efficacy in in vivo mouse models. In order to overcome these weaknesses, we newly synthesized aminopiperidine derivatives with remarkable antimicrobial properties and oral bioavailability, and also identified their in vivo efficacy against methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus (VRE) and penicillin-resistant Streptococcus pneumoniae (PRSP).

AZACYCLIC COMPOUNDS

Compounds and methods are provided for the treatment of disease conditions in which modification of serotonergic receptor activity has a beneficial effect. In the method, an effective amount of a compound is adminstered to a patient in need of such treatment.

USE OF 4-AMINO-PIPERIDINES FOR TREATING SLEEP DISORDERS

Inverse agonists and antagonists of serotonin receptors are disclosed for use in treating sleep disorders such as insomnia, and specifically sleep maintenance insomnia. The compound increase slow wave sleep, decrease the number of awakenings after sleep onset, and decrease the time awake after sleep onset.

INHIBITORS OF MONOAMINE UPTAKE

N,N-disubstituted 4-amino-piperidines of the general Formula (I) are inhibitors of the uptake of serotonin and/or norepinephrine and/or dopamine. As such, they may be useful for the treatment of disorders of the central and/or peripheral nervous system.

First dual NK1 antagonists-serotonin reuptake inhibitors: Synthesis and SAR of a new class of potential antidepressants

Compounds combining NK1 antagonism and serotonin reuptake inhibition are described, and potentially represent a new generation of antidepressants. Compound 24 displays good affinities for both the NK1 receptor and the serotonin reuptake site (32 and 25 nM, respectively).

Azacyclic compounds

Compounds and methods are provided for the treatment of disease conditions in which modification of serotonergic receptor activity has a beneficial effect. In the method, an effective amount of a compound is adminstered to a patient in need of such treatment.

Azetidine, pyrrolidine and piperidine derivatives

A class of substituted azetidine, pyrrolidine and piperidine derivatives are selective agonists of 5-HT1 -like receptors, being potent agonists of the human 5-HT1Dα receptor subtype whilst possessing at least a 10-fold selective affinity for the 5-HT1Dα receptor subtype relative to the 5-HT1Dβ subtype; they are therefore useful in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT1D receptors is indicated, whilst eliciting fewer side-effects, notably adverse cardiovascular events, than those associated with non-subtype-selective 5-HT1D receptor agonists.