79412-58-1

Upstream product

• 79601-23-3 1-<3-(3-methoxyphenyl)pyrrolidin-1-yl>propan-1-one 
• 766-85-8 3-methoxy-1-iodobenzene 
• 178483-02-8 1-(2,5-Dihydro-pyrrol-1-yl)-propan-1-one 
• 188196-65-8 1-[3-(3-Methoxy-phenyl)-2,3-dihydro-pyrrol-1-yl]-propan-1-one 
• 79-03-8 propionyl chloride 
• 38175-35-8 3-(3-methoxyphenyl)pyrrolidine 

Downstream Products

• 178483-00-6 USDA 19 
• 79412-59-2 3-(3-hydroxyphenyl)-N-n-propylpyrrolidine hydrobromide 

Relevant academic research and scientific papers

Regioselective synthesis of 3-aryl substituted pyrrolidines via palladium catalyzed arylation: Pharmacological evaluation for central dopaminergic and serotonergic activity

A series of 3-arylpyrrolidines has been synthesised via palladium catalyzed arylation and evaluated for dopaminergic and serotonergic activity in vitro and in vivo. Compounds substituted by electron withdrawing groups on the meta position of the aromatic ring, were found to be preferential dopamine autoreceptor antagonists.

Regiochemical control and suppression of double bond isomerization in the heck arylation of 1-(methoxycarbonyl)-2,5-dihydropyrrole

Arylation of 1-(methoxycarbonyl)-2,5-dihydropyrrole under standard Heck reaction conditions produces a mixture of compounds. The olefin undergoes two types of palladium-catalyzed reactions: (a) arylation to provide C-3 arylated derivatives and (b) competing double bond isomerization. Addition of silver carbonate and thallium acetate fully suppressed the isomerization, and good yields of C-3 substituted compounds were achieved after arylation with aryl halides. With regard to aryl triflates as arylating agents, addition of lithium chloride was necessary to promote the Heck reaction. This additive excluded the use of silver and thallium salts, but high regioselectivity and good yields could be obtained by employing tri-2-furylphosphine as ligand. Arylation was rendered both regioselective and enantioselective (58% ee) with 1-naphthyl triflate as substrate utilizing a (R)-BINAP/thallium acetate combination. The C-3 arylated enamides were converted further into the corresponding 3-arylpyrrolidines.

PHENYL-AZACYKLOALKANES

Compound of the formula STR1 wherein n is 1 or 2, Y is OH, R 1 COO--, R 2 R 3 NCOO--or R 4 O whereby R 1 is an alkyl group, or a possibly substituted phenyl group, R 2 is an alkyl, phenethyl, or benzyl or phenyl group, R 3 is H or an alkyl group and R 4 i

3-Phenylpiperidines. Central Dopamine-Autoreceptor Stimulating Activity

Thirty compounds related to the selective dopamine-autoreceptor agonist 3-(3-hydroxyphenyl)-N-n-propylpiperidine have been synthesized and tested for central dopamine-autoreceptor stimulating activity.The 3-(3-hydroxyphenyl)piperidine moiety seems indispensable for high potency and selectivity.Introduction of an additional hydroxyl group into the 4-position of the aromatic ring gives a compound with dopaminergic activity but lacking selectivity for autoreceptors. 3-(3-Hydroxyphenyl)-N-n-propylpyrrolidine, 3-(3-hydroxy)-N-n-propylperhydroazepine, and 3-(3-hydroxyphenyl)quinuclidine were all inactive.The most potent compounds were the N-isopropyl-, N-n-butyl-, N-n-pentyl-, and N-phenethyl-substituted 3-(3-hydroxyphenyl)piperidine derivatives.None of the compounds investigated seemed to have central noradrenaline- or serotonin-receptor stimulating activity.