1202-55-7

Upstream product

• 35256-93-0 N,N-dimethyl-4-phenylbutanamide 
• 13633-25-5 1-Bromo-4-phenylbutane 
• 3360-41-6 4-phenyl-butan-1-ol 
• 124-40-3 dimethyl amine 
• 300-57-2 allylbenzene 
• 107-31-3 Methyl formate 
• 1821-12-1 4-Phenylbutyric acid 
• 50-00-0 formaldehyd 
• 13214-66-9 4-phenyl-1-butylamine 

Downstream Products

• 3760-63-2 4-(dimethylamino)-1-phenylbutan-1-one 
• 60924-63-2 trimethyl-(4-phenyl-butyl)-ammonium; iodide 

Relevant academic research and scientific papers

Dimethylamination of Primary Alcohols Using a Homogeneous Iridium Catalyst: A Synthetic Method for N, N-Dimethylamine Derivatives

A new catalytic system for N,N-dimethylamination of primary alcohols using aqueous dimethylamine in the absence of additional organic solvents has been developed. The reaction proceeds via borrowing hydrogen processes, which are atom-efficient and environmentally benign. An iridium catalyst bearing an N-heterocyclic carbene (NHC) ligand exhibited high performance, without showing any deactivation under aqueous conditions. In addition, valuable N,N-dimethylamine derivatives, including biologically active and pharmaceutical molecules, were synthesized. The practical application of this methodology was demonstrated by a gram-scale reaction.

MANGANESE (III) CATALYZED C--H AMINATIONS

Reactions that directly install nitrogen into C—H bonds of complex molecules are significant because of their potential to change the chemical and biological properties of a given compound. Selective intramolecular C—H amination reactions that achieve high levels of reactivity, while maintaining excellent site-selectivity and functional-group tolerance is a challenging problem. Herein is reported a manganese perchlorophthalocyanine catalyst [MnIII(ClPc)] for intermolecular benzylic C—H amination of bioactive molecules and natural products that proceeds with unprecedented levels of reactivity and site-selectivity. In the presence of Br?nsted or Lewis acid, the [MnIII(ClPc)]-catalyzed C—H amination demonstrates unique tolerance for tertiary amine, pyridine and benzimidazole functionalities. Mechanistic studies indicate that C—H amination proceeds through an electrophilic metallonitrene intermediate via a stepwise pathway where C—H cleavage is the rate-determining step of the reaction. Collectively these mechanistic features contrast previous base-metal catalyzed C—H aminations.

Iron-catalyzed oxyfunctionalization of aliphatic amines at remote benzylic C-H sites

We report the development of an iron-catalyzed method for the selective oxyfunctionalization of benzylic C(sp3)-H bonds in aliphatic amine substrates. This transformation is selective for benzylic C-H bonds that are remote (i.e., at least three carbons) from the amine functional group. High site selectivity is achieved by in situ protonation of the amine with trifluoroacetic acid, which deactivates more traditionally reactive C-H sites that are α to nitrogen. The scope and synthetic utility of this method are demonstrated via the synthesis and derivatization of a variety of amine-containing, biologically active molecules.

Methylformate as replacement of syngas in one-pot catalytic synthesis of amines from olefins

A new general approach for the one-pot hydroaminomethylation of olefins using methylformate as formylating agent instead of synthesis gas (syngas) has been proposed. Herein we report that a Ru-Rh catalytic system demonstrates high activity in a tandem conversion of a series of n-alkenes into amines using methylformate with yields 58-92% (6 h). The selectivity for the normal amine reached 96% with catalysis by the Ru carbonyl complex Ru3(CO) 12, with an overall yield of 55% with respect to amine in this instance. The addition of the Rh complex to Ru catalytic system, sharply increased the hydroaminomethylation rate of both the terminal and internal alkenes and increased the yield of amines to 82-93% (6-12 h). The Royal Society of Chemistry.

Synthesis of quaternary alkylammonium sulfobetaines

A series of quaternary alkylammonium sulfobetaines of general formula RN+(CH3)2(CH2)nSO 3-, where n = 2-4, have been synthesised by reacting the corresponding N,N-dimethylamines with either sodium 2-chloroethanesulfonate (n = 2), 1,3-propane-sultone (n = 3), or 1,4-butanesultone (n = 4). Full details of the preparation of the required N,N-dimethylamines are reported.

Transformation of Monoamine Oxidase-B Primary Amine Substrates into Time-Dependent Inhibitors. Tertiary Amine Homologues of Primary AMine Substrates

A family of N-methylated and N,N-dimethylated alkyl and arylalkylamines was prepared and more than half of the analogues were shown to be time-dependent pseudo-first-order inhibitors of monoamine oxidase-B.Some of the time-dependent inactivators were reversible and others were irreversible with respect to prolonged dialysis following inactivation.Partition ratios ranged from zero to 11 000.These results are rationalized in terms of a combination of an inductive effect and a stereoelectronic effect as a result of hindered rotation of an active site covalent adduct.A molecualr mechanics calculation indicates that there is at least 10 kcal/mol of torsional energy to be overcome in order for the enzyme adduct to be released.These findings show that tertiary amine homologues of primary amine substrates of monoamino oxidase are time-dependent inhibitors, and this should be useful in the design of new inactivators of this enzyme.

Quaternary ammonium compounds having muscle relaxation activity

A quaternary ammonium having a muscle relaxation activity compound represented by the formula (I): STR1 wherein R1 represents a methylene, a lower alkylenoxy, a lower alkenylene, a lower alkynylene, --CO--, --COO--, a lower alkylene carbonyloxy, --CH(OR5)--, a lower alkylenecarbonyl, a hydroxy lower alkylene, --O--, --S--, --SO--, or --SO2 --; R2 represents a hydrogen atom, a hydroxy lower alkyl, an aldehyde, a lower alkyl carbonyl, --NO2, or --NHR6 ; R3 represents a hydrogen atom of a group --R1 --(CH2)a --[CH(CH2 A)--CH2 ]b --A; R4 represents an anion; R5 and R6 represent a hydrogen atom or a acetyl; A represents a quaternary ammonium group; a represents an integer of 1 to 8; b represents 0 or 1; m represents an integer of 1 to 4; and (Z) represents a trivalent benzene ring, a trivalent naphthalene ring, a trivalent diphenyl or a trivalent ethane radical.