50591-66-7

Basic information

• Product Name: 1-(2-Nitrobenzyl)piperidine
• Synonyms: 1-(2-Nitrobenzyl)piperidine
• CAS NO: 50591-66-7
• Molecular Formula: C₁₂H₁₆N₂O₂
• Molecular Weight: 220.27
• Mol File: 50591-66-7.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(2-Nitrobenzyl)piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-Nitrobenzyl)piperidine(50591-66-7)
• EPA Substance Registry System: 1-(2-Nitrobenzyl)piperidine(50591-66-7)

Safety Data

• Hazardous Substances Data: 50591-66-7(Hazardous Substances Data)

Upstream product

• 110-89-4 piperidine 
• 612-23-7 2-nitrobenzyl chloride 
• 5385-87-5 o-nitrobenzyl diazomethane 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 552-89-6 2-nitro-benzaldehyde 
• 1316859-98-9 potassium 2-(2-nitrophenyl)acetate 

Downstream Products

• 108619-23-4 8-piperidinomethyl-quinoline 
• 19577-83-4 2-(piperidin-1-ylmethyl)aniline 

Relevant articles and documents

Direct Catalytic Decarboxylative Amination of Aryl Acetic Acids

The decarboxylative coupling of a carboxylic acid with an amine nucleophile provides an alternative to the substitution of traditional organohalide coupling partners. Benzoic and alkynyl acids may be directly aminated by oxidative catalysis. In contrast, methods for intermolecular alkyl carboxylic acid to amine conversion, including amidate rearrangements and photoredox-promoted approaches, require stoichiometric activation of the acid unit to generate isocyanate or radical intermediates. Reported here is a process for the direct chemoselective decarboxylative amination of electron-poor arylacetates by oxidative Cu catalysis. The reaction proceeds at (or near) room temperature, uses native carboxylic acid starting materials, and is compatible with protic, electrophilic, and other potentially complicating functionality. Mechanistic studies support a pathway in which ionic decarboxylation of the acid generates a benzylic nucleophile which is aminated in a Chan–Evans–Lam-type process.

New phenylaniline derivatives as modulators of amyloid protein precursor metabolism

The chloroquinoline scaffold is characteristic of anti-malarial drugs such as chloroquine (CQ) or amodiaquine (AQ). These drugs are also described for their potential effectiveness against prion disease, HCV, EBV, Ebola virus, cancer, Parkinson or Alzheimer diseases. Amyloid precursor protein (APP) metabolism is deregulated in Alzheimer's disease. Indeed, CQ modifies amyloid precursor protein (APP) metabolism by precluding the release of amyloid-beta peptides (Aβ), which accumulate in the brain of Alzheimer patients to form the so-called amyloid plaques. We showed that AQ and analogs have similar effects although having a higher cytotoxicity. Herein, two new series of compounds were synthesized by replacing 7-chloroquinolin-4-amine moiety of AQ by 2-aminomethylaniline and 2-aminomethylphenyle moieties. Their structure activity relationship was based on their ability to modulate APP metabolism, Aβ release, and their cytotoxicity similarly to CQ. Two compounds 15a, 16a showed interesting and potent effect on the redirection of APP metabolism toward a decrease of Aβ peptide release (in the same range compared to AQ), and a 3–10-fold increased stability of APP carboxy terminal fragments (CTFα and AICD) without obvious cellular toxicity at 100 μM.

N-CARBOMETHOXY-N-METHOXY-(2-CHLOROMETHYL)-ANILINES, THEIR PREPARATION AND THEIR USE AS PRECURSORS FOR PREPARING 2-(PYRAZOL-3'-YLOXYMETHYLENE)-ANILIDES

The present invention relates to N-carbomethoxy-N-methoxy-(2-chloromethyl)-aniline compounds of the formula I, wherein: n is 0, 1, 2 or 3, each R1 is independently selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4- alkoxy or C1-C4-haloalkoxy. The invention also relates to processes and intermediates for preparing such compounds of formula I. The invention furthermore relates to processes for preparing 2-(pyrazol-3'-yloxymethylene)-anilides in which compounds of formula I are applied as precursors.