93172-46-4

Upstream product

• 107-31-3 Methyl formate 
• 25611-78-3 (R,S)-1,2-diphenylethylamine 
• 451-40-1 phenyl benzyl ketone 
• 77287-34-4 formamide 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 135365-08-1 5-Phenyl-6,10b-dihydro-5H-oxazolo[2,3-a]isoquinoline-2,3-dione 
• 135365-20-7 3,4-dihydro-3-phenylisoquinoline 
• 146530-25-8 2-formyl-1,2,3,4-tetrahydro-3-phenylisoquinoline 
• 25611-78-3 (R,S)-1,2-diphenylethylamine 

Relevant academic research and scientific papers

Synthesis and structure-activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores

Using N-(2,6-dimethyl)phenyl-2-piperidinecarboxamide (1) and N-(α-methylbenzyl)-2-piperidinecarboxamide (2) as structural leads, a variety of analogues were synthesised and evaluated for anticonvulsant activity in the MES test in mice. In the N-benzyl series, introduction of 3-Cl, 4-Cl, 3,4-Cl2, or 3-CF3 groups on the aromatic ring led to an increase in MES activity. Replacement of the α-methyl group by either i-Pr or benzyl groups enhanced MES activity with no increase in neurotoxicity. Substitution on the piperidine ring nitrogen led to a decrease in MES activity and neurotoxicity, while reduction of the amide carbonyl led to a complete loss of activity. Movement of the carboxamide group to either the 3- or 4-positions of the piperidine ring decreased MES activity and neurotoxicity. Incorporation of the piperidine ring into a tetrahydroisoquinoline or diazahydrinone nucleus led to increased neurotoxicity. In the N-(2,6-dimethyl)phenyl series, opening of the piperidine ring between the 1- and 6-positions gave the active norleucine derivative 75 (ED50 = 5.8 mg kg-1, TD50 = 36.4 mg kg-1, PI = 6.3). Replacement of the piperidine ring of 1 by cycloalkane (cyclohexane, cyclopentane, and cyclobutane) resulted in compounds with decreased MES activity and neurotoxicity, whereas replacement of the piperidine ring by a 4-pyridyl group led to a retention of MES activity with a comparable PI. Simplification of the 2-piperidinecarboxamide nucleus of 1 into a glycinecarboxamide nucleus led to about a six-fold decrease in MES activity. The 2,6-dimethylanilides were the most potent compounds in the MES test in each group of compounds evaluated, and compounds 50 and 75 should be useful leads in the development of agents for the treatment of tonic-clonic and partial seizures in man.

Towards the rehabilitation of the Leuckart reductive amination reaction using microwave technology

Leuckart reductive amination of carbonyl compounds was dramatically enhanced with respect to conventional heating by a specific microwave effect when the reaction was performed, under solvent-free conditions, in a monomode microwave reactor. Excellent iso

Application of the intramolecular ?-amidoalkylation reaction for the synthesis of 3- and 1,3-alkyl(aryl) 2-formyltetrahydroisoquinolines

3- and 1,3-alkyl(aryl) 2-formyltetrahydroisoquinolines 6 are obtained by the application of the intramolecular ?-amidoalkylation reaction from 1-alkyl(aryl)-2-arylethylformamides 2 and aldehydes in acidic medium.

Use of the N-formyliminium ion cyclization for the synthesis of 3-aryl-1,2,3,4-tetrahydroisoquinolines

Classical cyclization procedures for the synthesis of 3-arylisoquinolines are fraught with complications. Here, we present the application of an N-acyliminium cyclization to such target molecules. N(1,2-diarylethyl)formamides 1, 4a-4d, and 4f were cyclize

A Modified Bischler-Napieralski Procedure for the Synthesis of 3-Aryl-3,4-dihydroisoquinolines

A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented.Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3.Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields.The method is also highly effective with (2-phenylethyl)amides.