54105-61-2

Upstream product

• 119-65-3 isoquinoline 
• 622-24-2 2-phenylethyl chloride 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 103-63-9 1-phenyl-2-bromoethane 
• 30562-55-1 N-(2-Phenylethyl)-3,4-dihydroisochinolin-1(2H)-on 
• 95711-85-6 N-(2-Phenylethyl)-2-(2-hydroxyethyl)-benzamid 
• 103-82-2 phenylacetic acid 
• 100-42-5 styrene 
• 4702-34-5 isochroman-1-one 
• 10165-99-8 2-(2-Phenylethyl)-isocarbostyril 
• 64-04-0 phenethylamine 
• 82746-02-9 1-phenethylaminoisochroman 
• 1203602-82-7 (E)-N-styryl-1,2,3,4-tetrahydroisoquinoline 
• 60-12-8 2-phenylethanol 

Downstream Products

• 1312343-60-4 4-((5-methylfuran-2-yl)methyl)-2-phenethyl-1,2,3,4-tetrahydroisoquinoline 
• 1312343-61-5 4-hexyl-2-phenethyl-1,2,3,4-tetrahydroisoquinoline 
• 1370354-66-7 3-(5-((2-phenethyl-1,2,3,4-tetrahydroisoquinolin-4-yl)-methyl)furan-2-yl)benzonitrile 
• 1370354-68-9 4-((5-(naphthalen-1-yl)furan-2-yl)methyl)-2-phenethyl-1,2,3,4-tetrahydroisoquinoline 
• 1370354-70-3 4-((5-(4-nitrophenyl)furan-2-yl)methyl)-2-phenethyl-1,2,3,4-tetrahydroisoquinoline 
• 1370354-71-4 4-(5-((2-phenethyl-1,2,3,4-tetrahydroisoquinolin-4-yl)-methyl)thiophen-2-yl)benzaldehyde 
• 1370354-73-6 4-(5-((2-phenethyl-1,2,3,4-tetrahydroisoquinolin-4-yl)-methyl)thiophen-2-yl)benzonitrile 
• 1370354-74-7 3-(5-((2-phenethyl-1,2,3,4-tetrahydroisoquinolin-4-yl)-methyl)thiophen-2-yl)benzonitrile 
• 1370354-75-8 4-((5-(naphthalen-1-yl)thiophen-2-yl)methyl)-2-phenethyl-1,2,3,4-tetrahydroisoquinoline 
• 1370354-63-4 4-(5-((2-phenethyl-1,2,3,4-tetrahydroisoquinolin-4-yl)-methyl)furan-2-yl)benzaldehyde 
• 1370354-65-6 4-(5-((2-phenethyl-1,2,3,4-tetrahydroisoquinolin-4-yl)-methyl)furan-2-yl)benzonitrile 
• 1370354-62-3 4-(benzofuran-2-ylmethyl)-2-phenethyl-1,2,3,4-tetrahydroisoquinoline 
• 1370354-60-1 4-((3-methylthiophen-2-yl)methyl)-2-phenethyl-1,2,3,4-tetrahydroisoquinoline 
• 1370354-57-6 4-((1-methyl-1H-pyrrol-2-yl)methyl)-2-phenethyl-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of: In situ -formed enamines

A highly efficient B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of in situ-formed enamines in the presence of water and pinacolborane was developed. Regioselective β-deuteration of tertiary amines was achieved with high chemo- and regioselectivity. D2O was used as a readily available and cheap source of deuterium. Mechanistic studies indicated that B(C6F5)3 could activate water to promote the protonation and reduction of enamines. This journal is

Tropylium-Promoted Oxidative Functionalization of Tetrahydroisoquinolines

Structural modification of the tetrahydroisoquinoline (THIQ) framework is of significant interest to organic chemists due to its central role in heterocyclic and medicinal chemistry. Here we demonstrate an efficient metal-free method for the oxidative fun

Ru-catalyzed β-selective and enantioselective addition of amines to styrenes initiated by direct arene-exchange

A catalytic β-selective addition of amines to styrenes proceeded in the presence of cationic Ru complexes combined with diphosphine ligands. In the reaction of α-methylstyrene, an enantioselective addition was achieved by using xylylBINAP.

Sp3 C-H bond activation with ruthenium(II) catalysts and C(3)-alkylation of cyclic amines

A selective C(3)-alkylation via activation/functionalization of sp 3 C-H bond of saturated cyclic amines was promoted by (arene)ruthenium(II) complexes featuring a bidentate phosphino-sulfonate ligand upon reaction with aldehydes. This highly regioselective sustainable transformation takes place via initial dehydrogenation of cyclic amines and hydrogen autotransfer processes.

Broadening the scope of group 4 hydroamination catalysis using a tethered ureate ligand

(Chemical Equation Presented) A broadly applicable group-4-based precatalyst for the hydroamination of primary and secondary amines was developed. Screening experiments involving a series of amide and urea proligands led to the discovery of a tethered bis(ureate) zirconium complex with unprecedented reactivity in the intermolecular hydroamination of alkynes and the intramolecular hydroamination of alkenes. This catalyst system is effective with primary and secondary amines, 1,2-disubstituted alkenes, and heteroatom-containing functional groups, including ethers, silanes, amines, and heteroaromatics. The gem-disubstituent effect is not required for cyclization. The catalyst is generally regioselective for the anti-Markovnikov product of intermolecular alkyne hydroamination, and chemoselective for hydroamination over C-alkylation when forming 6- and 7-membered rings from aminoalkenes.

RUTHENIUM-CATALYZED HYDROAMINATION OF OLEFINS

Applicants have unexpectedly discovered that catalysts made from a ruthenium catalyst precursor or preformed ruthenium catalysts as otherwise described in the present specification are capable of effecting the addition of a N-H bond across an olefin C=C (olefinic) bond of a substrate with a high degree of regioselectivity and enantioselectivity in high yield. These addition reactions proceed in an anti-Markovnikov or Markovnikov fashion depending upon the catalyst precursor used to generate the ruthenium catalyst which actually participates in the addition reaction. The present invention relates to methods of adding N-H bonds across an olefinic bond in a substrate, using a ruthenium catalyst precursor or catalyst I comprising a compound according to the general structure I: Formula (I) where Ru is a ruthenium atom; L1 represents one or more coordinated ancillary ligands, which may be all the same ligand or which may be a combination of different ligands, each of which may be neutral or formally charged, and each of which may be monodentate and coordinated to ruthenium through a single atom or which may be linked or chelated and bound through more than one atom; L2 represents one or more formally charged ligands which are the same or different and which are optionally susceptible to removal with a strong acid; and x is 0-6, preferably 1, y is 0-6, preferably 2 and n is 1-4, preferably 1.

Ruthenium-Catalyzed Anti-Markovnikov Hydroamination of Vinylarenes

A ruthenium-catalyzed intermolecular, anti-Markovnikov hydroamination of vinylarenes with secondary aliphatic and benzylic amines is reported. The combination of Ru(cod)(2-methylallyl)2, 1,5-bis(diphenylphosphino)pentane, and triflic acid was the most effective catalyst of those tested. Control reactions conducted without ligand or acid did not form the amine. The reaction of morpholine, piperidine, 4-phenylpiperazine, 4-BOC-piperazine, 4-piperidone ethylene ketal, and tetrahydroisoquinoline with styrene in the presence of 5 mol % of this catalyst formed the corresponding β-phenethylamine products in 64?96% yield, with 99% regioselectivity, and without enamine side products. Acyclic amines such as n-hexylmethylamine and N-benzylmethylamine reacted with styrene in 63 and 50% yields, respectively. Alkyl-, methoxy-, and trifluoromethyl-substituted styrenes reacted with morpholine in the presence of this catalyst or a related one containing 1,1′-bis(diisopropylphosphino)ferrocene as ligand to give the products in 51?91%. Further, the hydroamination of α-methyl styrene was observed for the first time with a homogeneous transition metal catalyst. Preliminary mechanistic studies showed that the reaction occurred by direct, irreversible, anti-Markovnikov hydroamination and that the mechanism of the ruthenium-catalyzed hydroamination is likely to be distinct from that of the recently reported rhodium-catalyzed reaction. Copyright

N-nrylalkylpiperidines as high-affinity sigma-1 and sigma-2 receptor ligands: Phenylpropylamines as potential leads for selective sigma-2 agents

To delineate the differences between the structural requirements necessary for recognition at sigma-1 and sigma-2 receptors, a range of phenethyl- and phenylpropylpiperidines were evaluated in binding assays. Phenethylpiperidines were found to favor sigma-1 receptors, whereas phenylpropylpiperidines tend to favor sigma-2 receptors. It appears that phenylpropylamine is a potential pharmacophore for selective sigma-2 ligands.

Reductive amination of carboxylic acids and [11C]magnesium halide carboxylates

The reductive amination of carboxylic acids was shown to be promoted by 2-chloropyridine hydrochloride (3 eq). It allowed the one-pot preparation of N-alkylamines in yields up to 93% from carboxylic acid (1 eq), amine (1 eq) and sodium borohydride (5 molar eq). The reaction, carried out with [11C]magnesium halide carboxylates (11C, β+, t1/2:20 min), led to N-[11C]alkylamines in 20-25% radiochemical yields (decay corrected to the end of bombardment, 30 min preparation time from [11C]CO2). In this case, the addition of pyridinium salts led only to the corresponding [11C]carboxylic acids.

Structure-activity relationship studies of CNS agents, Part 23: N-(3-phenylpropyl)- and N-[(E)-cinnamyl]-1,2,3,4-tetrahydroisoquinoline mimic 1-phenylpiperazine at 5-HT1A receptors.

The 5-HT1A receptor affinities and ionization constants of a set of 1-arylpiperazine (4) 1,2,3,4-tetrahydroisoquinoline (6), and -quinoline (7) containing N-(omega-arylalkyl) or N-(E)-cinnamyl substituents as well as two morpholine derivatives (8a, 8b) we