87201-30-7

Basic information

• Product Name: N-<-2-(3,4-methylenedioxyphenyl)ethyl>-2'-bromophenylacetamide
• Synonyms: N-<-2-(3,4-methylenedioxyphenyl)ethyl>-2'-bromophenylacetamide
• CAS NO: 87201-30-7
• Molecular Weight: 362.223
• Mol File: 87201-30-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N-<-2-(3,4-methylenedioxyphenyl)ethyl>-2'-bromophenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-<-2-(3,4-methylenedioxyphenyl)ethyl>-2'-bromophenylacetamide(87201-30-7)
• EPA Substance Registry System: N-<-2-(3,4-methylenedioxyphenyl)ethyl>-2'-bromophenylacetamide(87201-30-7)

Safety Data

• Hazardous Substances Data: 87201-30-7(Hazardous Substances Data)

Upstream product

• 7154-66-7 2-bromobenzoic acid chloride 
• 18698-97-0 ortho-bromophenylacetic acid 
• 55116-09-1 2-bromophenylacetyl chloride 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 46004-44-8 2-bromo-ω-diazoacetophenone 

Downstream Products

• 548-08-3 (+)-roemerine 
• 76525-21-8 (2-bromophenyl)(7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methanone 
• 87489-86-9 1-(2'-bromo-α-hydroxybenzyl)-6,7-methylenedioxyisoquinoline 
• 87489-85-8 (2-bromophenyl)([1,3]dioxolo[4,5-g]isoquinolin-5-yl)methanone 
• 87201-32-9 ethyl (Z)-1-(2-bromobenzylidene)-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate 
• 934355-59-6 tert-butyl 5-(2-bromobenzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxylate 
• 934355-48-3 5-(2-bromobenzyl)-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline 
• 87201-31-8 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline 

Relevant articles and documents

Synthesis and evaluation of nuciferine and roemerine enantiomers as 5-HT2 and α1 receptor antagonists

In this study, the (S)-enantiomers of the aporphine alkaloids, nuciferine and roemerine, were prepared via a synthetic route involving catalytic asymmetric hydrogenation and both stereoisomers were evaluated in vitro for functional activity at human 5-HT2 and adrenergic α1 receptor subtypes using a transforming growth factor-α shedding assay. Both enantiomers of each of the compounds were found to act as antagonists at 5-HT2 and α1 receptors. (R)-roemerine was the most potent compound at 5-HT2A and 5-HT2C receptors (pKb = 7.8-7.9) with good selectivity compared to (S)-roemerine at these two receptors and compared to its activity at 5-HT2B, α1A, α1B and α1D receptors.

Aporphine alkaloid synthesis and diversification via direct arylation

Palladium-catalyzed direct arylation of aryl chlorides, bromides and iodides has been applied to the preparation of new aporphine analogues including C2-substituted aporphines by reaction with benzodioxole, pyridine N-oxide and pyrazine N-oxide. Successful application of direct arylation in these diversification reactions highlights its utility not only in convergent, but also in divergent synthesis. We also describe enantioselective syntheses of (R)-nornuciferine and (R)-nuciferine employing a catalytic asymmetric transfer hydrogenation in high yield and excellent enantiomeric excess. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Synthetic Photochemistry: Synthesis of Liriodenine

Bischler-Napieralski cyclisation of N--2'-bromophenylacetamide (3) followed by manganese dioxide oxidation of the crude amine (4) gives 1-(2'-bromobenzoyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline (5) which is aromatis