85660-33-9

Upstream product

• 102436-67-9 2-acetophenone 
• 70-11-1 α-bromoacetophenone 
• 56222-08-3 (2-nitrobenzyl)methylamine 
• 96-09-3 styrene oxide 

Downstream Products

• 89543-71-5 1-Butyl-3-(2-{[(2-hydroxy-2-phenyl-ethyl)-methyl-amino]-methyl}-phenyl)-urea 
• 89845-19-2 N-[2-ethoxycarbonylamino-benzyl]-1-phenyl-2-methyl-amino-1-ethanol 
• 99633-72-4 4-phenyl-8-<(chloroacetyl)amino>-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 24526-64-5 nomifensine 
• 65514-97-8 N-(2-Aminobenzyl)-2-(methylamino)-1-phenyl-1-ethanol 

Relevant academic research and scientific papers

An Improved Synthesis of 8-Amino-2-methyl-4-phenyl-1,2,3,4-Tetrahydroisoquinoline

The regioselectivity of the reaction of 2-nitrobenzylmethylamine (1) and styrenoxide (2) leading to a mixture of the isomeric aminoalcohols 3a and 3b has been studied.The course of the reaction strongly depends on the type of the solvent used as reaction medium.The highest selectivity (3a:3b=9:1) was achieved with a combination of polar aprotic and protic solvents (DMFA and ethanol). 1H n.m.r. spectroscopy was used for identification of the isomers as well as for the determination of their ratio in the crude reaction mixtures.The isomer ratio remains unaffected during catalytic reduction (Ra-Ni) of 3a/3b to a mixture of the correspondi ng aminoalcohols 4a and 4b.Pure 3a, 4a and 4b were independently synthesized for comparison.Cyclodehydration of crude 4a/4b mixtures gives 5 in a very good yield.

Synthesis and Pharmacological Evaluation of Some New Tetrahydroisoquinoline Derivatives Inhibiting Dopamine Uptake and/or Possessing a Dopaminomimetic Property

As shown by structure-activity relationship studies in 8-(substituted-amino)-4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinolines, the most important structural requirement for a marked antidepressant action is a presence of an ureido, (alkoxycarbonyl)amino, or amino group attached to the isoquinoline skeleton in position 8.In one of the biological test a significant difference was found between 8-amino-4-phenyl-2-methyl-1,2,3,4-tetrahydroisoquinoline (nomifensine) and the new compounds synthesized.Nearly all compounds substituted in the amino group either decrease the spontaneous motility in mice or exert no effect on it.Two syntheses have been elaborated for the preparation of the compounds represented by the general formulas II-V where R1 = hydrogen, halogen, or methyl; Y = CONHR, OCOR, or CO(CH2)nNHR, in which R = alkyl or aralkyl or NHR = cyclic amine and n = 1-2.The syntheses start either from the corresponding 8-amino-4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinolines or from the corresponding noncyclized amino alcohols.Of the compounds, 4-(p-chlorophenyl)-8--2-methyl-1,2,3,4-tetrahydroisoquinoline was found to possess the highest activity.