18780-56-8

Basic information

• Product Name: N-(3,4-dimethoxyphenethyl)-3,4-methylenedioxybenzamide
• Synonyms: N-(3,4-dimethoxyphenethyl)-3,4-methylenedioxybenzamide
• CAS NO: 18780-56-8
• Molecular Weight: 329.353
• Mol File: 18780-56-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(3,4-dimethoxyphenethyl)-3,4-methylenedioxybenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3,4-dimethoxyphenethyl)-3,4-methylenedioxybenzamide(18780-56-8)
• EPA Substance Registry System: N-(3,4-dimethoxyphenethyl)-3,4-methylenedioxybenzamide(18780-56-8)

Safety Data

• Hazardous Substances Data: 18780-56-8(Hazardous Substances Data)

Upstream product

• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 94-53-1 Piperonylic acid 

Downstream Products

• 111355-37-4 N-(3,4-methylenedioxybenzyl)-3,4-dimethoxyphenylethylamine 

Relevant articles and documents

Enantioselective Synthesis of 1-Aryl-Substituted Tetrahydroisoquinolines Through Ru-Catalyzed Asymmetric Transfer Hydrogenation

A convenient and general asymmetric transfer hydrogenation of a wide array of 1-aryl-3,4-dihydroisoquinoline derivatives using a [RuIICl(η6-benzene)TsDPEN] complex in combination with a 5:2 HCOOH-Et3N azeotropic mixture as a hydrogen source was developed. Under mild reaction conditions, the described catalytic transformation secured a practical synthetic access to the corresponding valuable chiral 1-aryltetrahydroisoquinoline units with high atom economy, a broad substrate scope, high isolated yields (up to 97%) and good to excellent enantioselectivities (up to 99% ee). It was found that the stereochemical outcome of the reaction was strongly influenced by both the structure of the catalyst and the substituents present on the substrate. The synthetic utility of the present protocol has been demonstrated through the asymmetric synthesis of several biologically important alkaloids including the antiepileptic drug agent 1c, as well as (-)-nor-cryptostyline alkaloids I and II.

Efficient and Practical Syntheses of Enantiomerically Pure (S)-(-)-Norcryptostyline I, (S)-(-)-Norcryptostyline II, (R)-(+)-Salsolidine and (S)-(-)-Norlaudanosine via a Resolution-Racemization Method

Four racemic tetrahydroisoquinolines (RS)-(±)-1-4 were prepared from homoveratrylamine via amidation, Bischler-Napieralski reaction and the subsequent reduction. The enantiomerically pure tetrahydroisoquinolines (S)- (-)-norcryptostyline I [(S)-(-)-1], (S)-(-)-norcryptostyline II [(S)-(-)-2], (R)-(+)-salsolidine [(R)-(+)-3] and (S)-(-)-norlaudanosine [(S)-(-)-4] were then obtained in 45%, 40%, 41% and 38% yields, respectively, via resolution of the racemic compounds (RS)-(±)-1-4 with half equivalent of chiral acids. In addition, the enantiomerically enriched compounds (R)-(+)-1, (R)-(+)-2, (S)-(-)-3 and (R)-(+)-4 from the mother liquors were efficiently racemized via a one-pot redox method in almost quantitative yields.