An efficient and mild route for the formation sulfur or phosphor-substituted alkynes was herein demonstrated. The Mukaiyama reagent-mediated transformation started from easily-accessible substrates without carbon-carbon triple bonds, and the reaction proceeded under mild conditions (room tempera...

Reaction of azulene (1) with 1,2-bis[4-(dimethylamino)phenyl]-1,2-ethanediol (2) in a mixed solvent of methanol and acetonitrile in the presence of 36% hydrochloric acid at 60 °C for 3 h gives 2-(azulen-1-yl)-1,1-bis[4-(dimethylamino)phenyl]ethylene (3) (8% yield), 1-(azulen-1-yl)-(E)-1,2-bis[4...

Although reaction of guaiazulene (1a) with 1,2-diphenyl-1,2-ethanediol (2a) in methanol in the presence of hydrochloric acid at 60 °C for 3 h under aerobic conditions gives no product, reaction of 1a with 1,2-bis(4-methoxyphenyl)-1,2-ethanediol (2b) under the same reaction conditions as 2a give...

Reaction of a bulky Schiff base, 2,6-dibenzhydryl-N-4-((2,6-dibenzhydryl-4-methylphenyl)imino)pent-2-en-2-yl)-4-methylaniline (Ar2NacNacH (Ar = 2,6-dibenzhydryl-4-methylphenyl)) with PdCl2 in toluene under reflux condition affords dinuclear [(Ar2NacNac)Pd (μ-Cl)]2 (1). Complex 1 upon crystalliz...

In this communication we report a convenient reduction technique for conversion of electron deficient aromatic nitro compounds to corresponding amino derivatives using hydrazine hydrate without any metal catalyst. The reduction process is carried out in different solvents under heating condition...

Synthesis of poly-substituted 3-hydroxy-2-oxindole-pyridine hybrids is reported via sp3 CH bond functionalization as key steps using FeWO4 nanoparticles as reusable heterogeneous catalyst. Formation of Hantzsch ester (DHP) followed by aromatization, and sp3 CH bond functionalization was achieved...

The discovery of novel and selective small molecule antagonists of the CC Chemokine Receptor-3 (CCR3) is presented. Simple conversion from a 4- to 3-benzylpiperidine gave improved selectivity for CCR3 over the serotonin 5HT2A receptor. Chiral resolution and exploration of mono- and disubstitutio...

Conformational analysis of the 3-benzylpiperidine in CCR3 antagonist clinical candidate 1 (BMS-639623) predicts that the benzylpiperidine may be replaced by acyclic, conformationally stabilized, anti-1,2-disubstituted phenethyl- and phenpropylamines. Ab initio calculations, enantioselective synt...

Some novel coumarin-3-carboxamide derivatives linked to N-benzylpiperidine scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The screening results showed that most of compounds exhibited potent anti-AChE activity in the range of ...

The present study describes aza-Michael addition reactions of 4-aroylpent-4-enoic acids with (R)-phenylglycinol. Subsequent spontaneous lactamization yielded the corresponding piperidin-2-ones, which can selectively crystallize in very high diastereomeric purity. These are useful intermediates i...

The agonist actions of 3-PPP at central dopamine (DA) autoreceptors were found to reside mostly in its (+) enantiomer. (+)-3-PPP also reduced striatal content of DOPAC and HVA, whereas (-)-3-PPP elevated HVA levels. Only (-)-3-PPP antagonized DA stimulation of DA-receptor linked adenylate cyclas...

The caudate spindle in rats was observed following bilateral application of apomorphine (1.5–50 μg) and (±)-3-(3-hydroxyphenyl)-N-n-propylpiperidine (3-PPP, 0.3–3 μg) into the striatum. The smallest dose (1.5 μg) of apomorphine enhanced the spindle whereas with a larger dose (50 μg), supp...

Background: In an ongoing effort to characterize the clinical pharmacologic profile of the partial dopamine agonist (−)-3-(3-hydroxyphenyl)-N-n-propylpiperidine [(−)-3PPP], we administered it to drug-free schizophrenic patients in two consecutive studies.Methods: In a preliminary dose-finding st...

The synthesis of the two enantiomers of 3-(3,4-dimethylphenyl)-1-propylpiperidine 1, a potent and selective D4 dopaminergic ligand, was performed. The 3-(3,4-dimethylphenyl)-1-propylpiperidine with the R configuration showed an affinity for the D4 receptors 6-fold higher than the corresponding e...

Bilateral injection of apomorphine into the zona reticulata of substantia nigra in rats reduced locomotor activity and striatal dopamine (DA) turnover. In contrast, bilateral injection of (±)-3-(3-hydroxyphenyl)-N,n-propylpiperidine [(±)-3-PPP] into the zona reticulata (ZR) did not reduce loco...

Reaction of (R)-phenylglycinol with racemic methyl 4-formylhexanoate takes place with a remarkable stereoselectivity to give two diastereomeric 6-ethyloxazolopiperidones (9:1 ratio) in 76% overall yield. After LiAlH4 reduction and catalytic hydrogenation, the major isomer was converted to (S)-3-...

A complete product study of the reaction of 3-chloro-1-ethylpiperidine (1) in aqueous sodium-hydroxide showed the formation of three bis-(β-aminoethers), 2,2′-bis-(N-ethyl-2-pyrrolidinomethyl) ether (6), 3-(N′-ethyl-2′-pyrrolidinomethoxy)-N-ethylpiperidine (7) and 3,3′-bis-N-ethyl-3-piperid...

The rate of the thermal rearrangement of (S) 2 chloromethyl-1-ethylpyrrolidine [(S)-1a] to (R)-3-chloro-1-ethylpiperidine [(R) 2a] has been examined at three temperatures in benzene by PMR and polarimetry. The rearrangement was shown to be completely stereospecific and to obey a simple first ord...

Synthetic, kinetic and optical activity studies have established that 3-chloro-1-ethylpiperidine undergoes nucleophilic displacement reactions in solution by a two-step, neighboring group participation mechanism. Nitrogen displaces chloride internally, to give an ambident bicyclic aziridinium io...

N-ethylpiperidine betaine, (N-carboxymethyl-N-ethylpiperidinium inner salt, EtPB) crystallizes as a hydrate. EtPB and water molecules are bonded by intermolecular OH⋯O hydrogen bonds of 2.817(1) and 2.863(1) Å, into a centrosymmetric dimer, in which only one carboxylate oxygen atom is involved i...