2538-76-3

Basic information

• Product Name: Bis(1-piperidinyl)phenylmethane
• Synonyms: 1,1'-Benzylidenedipiperidine;Bis(1-piperidinyl)phenylmethane
• CAS NO: 2538-76-3
• Molecular Formula: C₁₇H₂₆N₂
• Molecular Weight: 258.4017
• Mol File: 2538-76-3.mol

Chemical Properties

• Boiling Point: 340.2°Cat760mmHg
• Flash Point: 145.9°C
• Appearance: /
• Density: 1.047g/cm³
• CAS DataBase Reference: Bis(1-piperidinyl)phenylmethane(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(1-piperidinyl)phenylmethane(2538-76-3)
• EPA Substance Registry System: Bis(1-piperidinyl)phenylmethane(2538-76-3)

Safety Data

• Hazardous Substances Data: 2538-76-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 17, p. 32, 1969 DOI: 10.1248/cpb.17.32

Upstream product

• 110-91-8 morpholine 
• 100-52-7 benzaldehyde 
• 110-89-4 piperidine 
• 811-98-3 d⁽⁴⁾-methanol 
• 121238-80-0 N-<α-(benzotriazol-1-yl)phenylmethyl>piperidine 
• 3768-56-7 1-(trimethylsilyl)piperidine 
• 1865-47-0 piperidine sodium 
• 122699-86-9 1-(Bromo-phenyl-methyl)-pyridinium; bromide 
• 4222-25-7 3-bromo-3-phenyl-3H-diazirine 
• 92-29-5 hydrobenzamide 

Downstream Products

• 29976-76-9 8-bromo-6-methyl-2-phenyl-chromen-4-one 
• 35278-83-2 1-(1-phenylbut-3-en-1-yl)piperidine 
• 38608-50-3 3-(phenyl(piperidin-1-yl)methyl)pyridine 
• 1082512-40-0 2-methyl-4-phenyl-4-piperidino-1-butene 
• 1409957-07-8 1-(2,2-difluoro-1-phenyl-2-(phenylsulfonyl)ethyl)piperidine 
• 94533-57-0 meso-N,N,N',N'-bis(pentamethylen)-1,2-diphenylaethylendiamin 
• 94533-64-9 (+/-)-N,N,N',N'-bis(pentamethylen)-1,2-diphenylaethylendiamin 
• 1082512-39-7 3,3-dimethyl-4-phenyl-4-piperidino-1-butene 
• 120173-16-2 ethyl 3-phenyl-3-piperidinopropanoate 
• 36794-52-2 (±)-1-(1,2-diphenylethyl)piperidine 
• 55837-14-4 ethyl 3-phenyl-3-piperidinopropanoate 
• 1165-06-6 Diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 119569-83-4 3,13-dibenzylidene-cyclotridecane-1,2-dione 
• 102952-61-4 3,11-dibenzylidene-cycloundecane-1,2-dione 

Relevant articles and documents

S,S-Complexes of Copper(I) Halides with 1,2-Bis(3,5-dimethyloxazol-4-ylmethylsulfanyl)ethane as New Catalysts for Phenylacetylene Aminomethylation

New metal–heterocycle S,S-complexes based on Cu(I) binary halides and a polydentate ligand, 1,2- bis(3,5-dimethyloxazol-4-ylmethylsulfanyl)ethane have been prepared. The obtained complexes have demonstrated high catalytic activity in aminomethylation of p

SYNTHESIS OF AZONIA DERIVATIVE OF HEXAHELICINE

The azonia derivative of hexahelicine, 4a-azoniaphenanthrophenanthrene perchlorate, has been synthesized by photo-cyclization of 2-styrylnaphthoquinolizinium perchlorate.

Atom-efficient transition-metal-free arylation ofN,O-acetals using diarylzinc reagents through Zn/Zn cooperativity

Exploiting the cooperative action of Lewis acid Zn(C6F5)2with diarylzinc reagents, the efficient arylation ofN,O-acetals to access diarylmethylamines is reported. Reactions take place under mild reaction conditions without the need for transtion-metal catalysis. Mechanistic investigations have revealed that Zn(C6F5)2not only acts as a Lewis acid activator, but also enables the regeneration of nucleophilic ZnAr2species, allowing a limiting 50 mol% to be employed.

Rediscovering aminal chemistry: Copper(ii) catalysed formation under mild conditions

Aminals, the N,N analogues of acetals, have been thoroughly explored in organic chemistry, with a particular focus on heteroaromatic aldehyde lithiation. Nevertheless, the existing methodologies for their formation typically employ harsh conditions limiting their usefulness. In this work, we present an efficient and mild methodology for the preparation of aminals from aromatic aldehydes, including furanic platforms. These mild conditions allowed ease of access to a plethora of aminals and as such we set out to explore previously unaccessible potential applications. By studying the stability of various aminals, we were able to develop a simple aldehyde protecting group based on a commercial diamine which is deprotected under mind conditions. We developed a protocol for the scavenging of genotoxic aldehydes by taking advantage of our methodology and a diamine resin, as well as early studies on the development of a stimuli-responsive release system using a salycil aldehyde derived aminal. This journal is

Zinc-mediated allylation and alkylation of aminals in the presence of TMSCl and diisopropylamine

(Chemical Equation Presented) An alkylation of aminals with organozinc reagents derived from allyl bromide, benzyl bromide, α-bromoacetate, and α-bromonitrile proceeded efficiently in the presence of TMSCl and diisopropylamine. This reaction system was applied to the synthesis of an antispasmodic: butaverine.

CHEMICAL PROCESSES AND COMPOUNDS DERIVED THEREFROM

The present invention relates to N-substituted anilines and derivatives thereof and in particular to chemical processes for the preparation of N-substituted anilines and derivatives thereof.

A new protocol for the preparation of aminals from aromatic aldehydes and their facile conversion to phosphonates

A new and fast method for the preparation of aminals is reported from the reaction of aromatic aldehydes and secondary amines in the presence of potassium carbonate in high yields. The aminal can be converted to the corresponding iminum salt in reaction with acetyl chloride very easily and in very short time with high yield. Addition of trialkylphosphite, as one possible nucleophile, to the prepared iminium salt produces the α-amino phosphonate in very high yield.

A Scrutiny on the Reductive Amination of Carbonyl Compounds Catalyzed by Homogeneous Rh(I) Diphosphane Complexes

The reductive amination of a series of aldehydes with secondary amines and H2 in the presence of a homogeneous Rh-diphosphane catalyst was studied in order to establish a general mechanism of this reaction and to identify conditions for the improvement of the amine/alcohol ratio in the product. Several possible intermediates as constituents of changing equilibria like half-aminals, N,O-acetals and aminals were observed in the reaction mixture by means of 1H NMR spectroscopy. In individual trials, these compounds could be successfully hydrogenated under the conditions applied for reductive amination (50 bar H2 pressure, MeOH). Some evidence is accumulated that half-aminals and N,O-acetals might be key intermediates of the reductive amination. Moreover, it was found that the formation of the undesired product alcohol is likely based on the reduction of the starting carbonyl compound. However, due to numerous equilibria consisting of several intermediates, general conclusions are hard to be drawn. Proof will be given that, in several cases, the efficiency of the reductive amination of aliphatic aldehydes can be significantly improved by prehydrogenation of the cationic [Rh(dppb)(COD)]+ complex.

Aminal Exchange

Reactions of N-(α-benzotriazolylalkyl)-N,N-dialkylamines with the dialkylamine corresponding to the dialkylamino substituent afford symmetrical aminals in good yields.Treatment with other dialkylamines gives mixtures of the unsymmetrical and the two symme

SYNTHESIS OF 6-METHYLISOQUINOLINOQUINOLIZINIUM SALT: EFFICIENT SYNTHESIS OF 2-(2-ARYLVINYL)QUINOLIZINIUM SALTS BY KNOEVENAGEL CONDENSATION USING ACETONITRILE AS A SOLVENT AND THE PHOTOCYCLIZATION

In the Knoevenagel condensation of 2,3-dimethylquinolizinium salt with a vide variety of aromatic aldehydes in the presencce of piperidine, the use of acetonitrile as a solvent gave excellent yields (77-100percent) of 2-(2-arylvinyl)-quinolizinium salts.I