Über Alkylenimin‐Derivate. II Mitteilung. Piperidin‐Derivate mit zentralerregender Wirkung I

Abstract

Der Vergleich zeigt, dass im allgemeinen die Dehydrierung mit Schwefelkohlenstoff an Molybden-Nickelsulfid-Katalysatoren unter gunstigeren Bedingungen verlauft. Es besteht jedoch die Moglichkeit, dass andere Substanzen ein ungiinstigeres Bild ergeben wiirdenl).Der eine von urn (E. K.) dankt der Firma Hoffmann-La Roche in Base1 fiir die Unterstiitzung dieser Arbeit.SUMMARY.The catalytic dehydrogenation using carbon disulfide and a molybdenum-nickelsulfide catalyst on alumina carrier has been investigated, using as a testreaction the formation of azulene from A 1*7-bicyclo-[0,3, 51-decene:Maximum yields in the region of 6 0 % have been obtained. The dependence of the yield on different variables has been discussed using statistical methods.

Slow-Onset, Long-Duration, Alkyl Analogues of Methylphenidate with Enhanced Selectivity for the Dopamine Transporter

“…On the basis of this ligand-based design, we have synthesized methylphenidate analogues in which the carbomethoxy group is replaced by various alkyl groups. There has been one previous limited report of alkyl analogues of methylphenidate from a half-century ago in which there was apparently no separation of diastereomers . This was also prior to the development of binding and uptake assays so that it was impossible to determine any kind of selectivity, and in any case, virtually no in vivo pharmacological data were reported.…”

“…There has been one previous limited report of alkyl analogues of methylphenidate from a half-century ago in which there was apparently no separation of diastereomers. 21 This was also prior to the development of binding and uptake assays so that it was impossible to determine any kind of selectivity, and in any case, virtually no in vivo pharmacological data were reported. It should also be noted that the pharmacophore model for methylphenidate has been used by others to design novel methylphenidate analogues 22 and that the model has been successfully extended to the DA reuptake inhibitors bupropion 23 and BTCP.…”

Multigram Synthesis of α‐ and γ‐((Hetera)cyclo)alkylpyridines through α‐Arylation of (Hetero)aliphatic Nitriles

“…Next, we have aimed at the transformation of the synthesized nitriles into corresponding ((hetera)cyclo)alkylpyridines (Scheme 2). According to the literature data, a base‐promoted hydrolysis of nitrile moiety in compounds 3 requires rather harsh reaction conditions (KOH, MeOH, 215–225 °C) [39] . After several optimization experiments performed with substrate 3 v (Table S1 in the Supporting Information), we have found that the hydrolysis itself can be performed in ethylene glycol at 160 °C (conditions A ) or 1,4‐dioxane at 110 °C (conditions B ).…”

“…According to the literature data, a base-promoted hydrolysis of nitrile moiety in compounds 3 requires rather harsh reaction conditions (KOH, MeOH, 215-225 °C). [39] After several optimization experiments performed with substrate 3 v (Table S1 in the Supporting Information), we have found that the hydrolysis itself can be performed in ethylene glycol at 160 °C (conditions A) or 1,4-dioxane at 110 °C (conditions B). In both cases, carboxylic acid 6 a could not be isolated in pure form due to its partial decarboxylation providing target pyridine derivative 7 a.…”

The Synthesis of (±), (+) and (-) α-(3- Thiamorpholinyl)-benzhydrol, a New Selective Stimulant of the Central Nervous System

“…Along this line of research, methyl a-(2-piperidyl)-phenylacetate (methylphenidate) (II)f has also been recently proposed as a CNS stimulant5'6 and would appear to confirm the potentialities of piperidine derivatives in this respect. 7 The pharmacology of these drugs present several points of interest, the most striking being the selectivity of action which serves to establish that the central and peripheral actions of sympathomimetics can be dissociated. This suggested to us that a greater selectivity of action and a narrower spectrum of pharmacological activity might be achieved through appropriate chemical modification of the pipradrol molecule.…”