346688-61-7Relevant articles and documents
Optimizing the Mizoroki–Heck reaction of cyclic allyl amines: Gram-scale synthesis of preclamol without protecting groups
Sweeney, Joseph B.,Adams, Kirsty,Doulcet, Julien,Thapa, Bimod,Tran, Fanny,Crook, Robert
, p. 97 - 101 (2018)
Though a widely used metal-catalyzed cross-coupling process, the Mizoroki–Heck (MH) reaction can be a capricious transformation. This is particularly true for oxidation-prone alkene substrates containing ligating heteroatoms, as in the case of N-alkyl tetrahydropyridines, whose MH reactions have been underexplored due to the many side reactions that hamper the process. Since the products of tetrahydropyridine Heck reactions are direct precursors to potent pharmacophores, and therefore of commercial value, this is a significant drawback. We report here the results of our study designed to deliver an optimized, scalable MH procedure for N-alkyltetrahydropyridines and its exemplification in a gram-scale synthesis of the drug substance preclamol.
Synthesis and evaluation of a set of 4-Phenylpiperidines and 4-Phenylpiperazines as D2 receptor ligands and the discovery of the dopaminergic stabilizer 4-[3-(Methylsulfonyl)phenyl]-l-propylpiperidine (huntexil, pridopidine, ACR16)
Pettersson, Fredrik,Ponten, Henrik,Waters, Nicholas,Waters, Susanna,Sonesson, Clas
supporting information; experimental part, p. 2510 - 2520 (2010/08/22)
Modification of the partial dopamine type 2 receptor (D2) agonist 3-(l-benzylpiperidin-4-yl)phenol (9a) generated a series of novel functional D2 antagonists with fast-off kinetic properties. A representative of this series, pridopid
