846601-41-0

Upstream product

• 3490-06-0 N-methylhomoveratrylamine 
• 154138-43-9 2,2,2-trifluoro-N-<2-(2-iodo-4,5-dimethoxyphenyl)ethyl>acetamide 
• 13230-71-2 N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide 
• 1357480-92-2 N-methyl-N-(2-iodo-4,5-dimethoxyphenethyl)trifluoroacetamide 

Downstream Products

• 846601-44-3 3-(3,4-dimethoxyphenyl)-2-{[2-(2-iodo-4,5-dimethoxyphenyl)ethyl]methylamino}propionitrile 
• 1699-51-0 laudanosine 
• 3423-13-0 1-benzyl-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Phosphane-free Pd0-catalyzed cycloamination and carbonylation with Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3: Preparation of benzocyclic amines and benzolactams

Phosphane-free Pd0-catalyzed intramolecular aromatic amination was studied. o-Halophenethylamines and 3-(o-halophenyl)propylamines were found to be transformed into indolines and quinolines in a catalytic system based on Pd(OAc)2 and Cu(OAc)2 in the presence of K 2CO3. Application of the method to substrates containing isoquinoline rings- the 1-(o-bromobenzyl)-3,4-dihydroisoquinolines 6, the 1-(o-bromobenzyl)-1,2,3,4-tetrahydroisoquinolines 7, and the 1-(o-bromophenethyl)isoquinolines 9- provided the indolo[2,1-a]isoquinoline and dibenzo[a,f]quinolizine ring systems 8 and 10. Extension of the method to β-carbolines (compounds 11, 12, and 17) produced the benz[f]indolo[2,3-a] indolizine-13-ones 15 and the benz[f]indolo[2,3-a]quinolizine 18. The benzo[f]pyrido[3,4-a]indolizine and indolo[f]pyrido[3,4-a]indolizin-12-one ring systems 27 and 31 were built in a similar manner. It was also found that under an atmosphere of CO the same catalytic system produced the corresponding benzolactams, the isoquino[2,1-a][2,7]naphthyridine 34 and the indolo[2,3-a]pyrido[g]quinolizin-8-one 36 [(±)-dihydronauclefine] in good yields. Copyright

A convenient synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines by combined Strecker/Bruylants reaction

Strecker reaction of iodophenethylamines with phenylacetaldehydes afforded the corresponding α-aminonitriles, which on treatment with i-propyl magnesium chloride underwent a Bruylants reaction to give the title compounds. Their structures were deduced by NMR and by an independent preparation starting from papaverine. The educts were easily available by standard procedures. Springer-Verlag 2004.