3426-08-2

Usage

InChI:InChI=1/C21H27N/c1-2-10-17-22(16-9-1)18-15-21(19-11-5-3-6-12-19)20-13-7-4-8-14-20/h3-8,11-14,21H,1-2,9-10,15-18H2

Upstream product

• 89787-70-2 3-hexahydroazepin-1-yl-1,1-diphenyl-propan-1-ol 
• 83898-29-7 4-hexahydroazepin-1-yl-2,2-diphenyl-butyronitrile 
• 111-49-9 hexamethylene imine 
• 530-48-3 1,1-Diphenylethylene 
• 201230-82-2 carbon monoxide 
• 71-43-2 benzene 
• 571246-03-2 N-cynnamylhexamethyleneimine 
• 39186-58-8 4-bromo-2,2-diphenylbutyronitrile 
• 20017-67-8 3,3-diphenylpropan-1-ol 
• 4279-81-6 3,3-diphenylpropanal 
• 86-29-3 Diphenylacetonitrile 
• 4392-24-9 Cinnamyl bromide 
• 15391-79-4 3-azepan-1-yl-1-phenyl-propan-1-one 
• 6763-93-5 3-hexahydroazepin-1-yl-propionic acid ethyl ester 

Downstream Products

• 114036-11-2 1-(3,3-diphenyl-propyl)-1-methyl-hexahydro-azepinium; iodide 

Relevant academic research and scientific papers

One-pot synthesis of pharmacologically active secondary and tertiary 1- (3,3-diarylpropyl)amines via rhodium-catalysed hydroaminomethylation of 1,1- diarylethenes

Pharmacologically active secondary and tertiary 1-(3,3- diarylpropyl)amines 1 are prepared in high yields and chemoselectivity by the reaction of 1,1-diarylethenes 4, primary or secondary amines 5, carbon monoxide and hydrogen in presence of [Rh(cod)Cl]2/PBu3 as catalyst via a one-pot hydroformylation - amine condensation - reduction sequence.

Chemoselective Reductive Aminations in Aqueous Nanoreactors Using Parts per Million Level Pd/C Catalysis

Condensation in recyclable water between aldehydes or ketones and amines occurs smoothly within the hydrophobic cores of nanomicelles, resulting in imine formation that is subject to subsequent reduction leading, overall, to reductive amination. This micellar technology enables the synthesis of several types of pharmaceuticals, a new procedure that relies on only 2000 ppm (0.20 mol %) palladium from commercially available Pd/C. A broad range of substrates can be used under mild conditions, leading to high chemical yields of the desired secondary and tertiary amines.

Migratory Arylboration of Unactivated Alkenes Enabled by Nickel Catalysis

An unprecedented arylboration of unactivated terminal alkenes, featuring 1,n-regioselectivity, has been achieved by nickel catalysis. The nitrogen-based ligand plays an essential role in the success of this three-component reaction. This transformation displays good regioselectivity and excellent functional-group tolerance. In addition, the incorporation of a boron group into the products provides substantial opportunities for further transformations. Also demonstrated is that the products can be readily transformed into pharmaceutically relevant molecules. Unexpectedly, preliminary mechanistic studies indicate that although the metal migration favors the α-position of boron, selective and decisive bond formation is favored at the benzylic position.

Benzimidazolin-2-ylidene N-heterocyclic carbene complexes of ruthenium as a simple catalyst for the N-alkylation of amines using alcohols and diols

Simple air and moisture stable ruthenium complexes 1-3 and 3a were synthesized from readily available benzannulated N-heterocyclic carbene ligands (bimy = benzimidazolin-2-ylidene). These complexes were found to be efficient catalysts for the alkylation of amines using alcohols as alkylating agents. Catalysts 1, 2 and 3a gave excellent yields of up to 99% for the alkylation of various amines using benzylic and aliphatic alcohols at 130 °C for 18 h under solventless conditions. Catalyst 3a bearing both phosphine and carbene ligands gave excellent yields of up to 98% for the synthesis of heterocyclic amines by double alkylation of primary amines using linear diols. The practical utility of these catalysts was demonstrated for the synthesis of pharmaceutically important amines in a more environmentally benign way under solventless conditions.

Cascade synthesis of fenpiprane and related pharmaceuticals via rhodium-catalyzed hydroaminomethylation

A novel rhodium catalytic system with Naphos as ligand was developed for an efficient hydroaminomethylation of 1,1-diphenylethene under relatively mild conditions. This will allow for an atom-economic and environmentally benign synthesis of fenpiprane and related pharmaceuticals.

Hydroaminomethylation with novel Rhodium-Carbene complexes: An efficient catalytic approach to pharmaceuticals

Starting from [{Rh(cod)Cl}2] and 1,3-dimesitylimidazole-2- ylidenes the novel [RhCl(cod)(carbene)] complexes 1-5 have been synthesized, characterized, and tested in the hydroaminomethylation of aromatic olefins. The influence of different ligands and reaction parameters on the catalytic activity was investigated in detail applying 1,1-diphenylethylene and piperidine as a model system. The scope and limitations of the novel catalysts is shown in the preparation of 16 biologically active 1-amino-3,3-diarylpropenes. In general, high chemo- and regioselectivity as well as good yields of the desired products were achieved.

Dicationic electrophiles from olefinic amines in superacid

This paper describes the superacid-catalyzed chemistry of olefinic amines and related compounds. A variety of olefinic amines are found to react with benzene in CF3SO3H (triflic acid) to give addition products in good yields (75-99%), including the pharmaceutical agents fenpiprane and prozapine. A general mechanism is proposed that invokes the formation of reactive, dicationic electrophiles and the direct observation of a diprotonated species is reported from low-temperature NMR experiments. This chemistry is also used to conveniently prepare functionalized polystyrene beads having pendant amine groups.

Chemistry of dicationic electrophiles: superacid-catalyzed reactions of amino acetals.

Amino acetals are shown to form highly electrophilic systems in Bronsted superacids. It is proposed that amino acetals give dicationic electrophiles, and this proposal is supported by the direct observation of a dication by low-temperature (13)C NMR. When reacted with C(6)H(6) and superacidic CF(3)SO(3)H, amino acetals are shown to provide 1-(3,3-diphenylpropyl)amines and 1-(2,2-diphenylethyl)amines as condensation products in good yields (50-99%).

Process for the preparation of tertiary amines

Certain tertiary amines useful as pharmaceuticals are prepared in improved yields by condensing a cyclic secondary amine with a primary alkyl halide in an aqueous medium in the presence of an acid acceptor.