Heterocyclic Building Blocks-piperidine

Crich, David published the artcile1-benzenesulfinyl piperidine (BSP)/triflic anhydride. An effective combination for the hydrolysis of dithioacetals, Related Products of piperidines, the publication is Synlett (2003), 1257-1258, database is CAplus.

The combination of 1-benzenesulfinyl piperidine and triflic anhydride, in conjunction with an aqueous workup, hydrolyzes a broad range of dithioacetals to the corresponding carbonyl compounds under very mild, non-oxidative conditions.

Synlett published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, Related Products of piperidines.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Crich, David published the artcileDirect Synthesis of the β-L-Rhamnopyranosides, Name: 1-(Phenylsulfinyl)piperidine, the publication is Organic Letters (2003), 5(5), 781-784, database is CAplus and MEDLINE.

The direct formation of β-L-rhamnopyranosides by means of thioglycoside donors protected with a 2-O-sulfonate ester and, ideally, a 4-O-benzoyl ester, is reported. Activation is achieved with the combination of 1-benzenesulfinyl piperidine and triflic anhydride in the presence of 2,4,6-tri-tert-butylpyrimidine. Selectivities vary from moderate to good, and the sulfonyl group is easily removed post-glycosylation with sodium amalgam in 2-propanol.

Organic Letters published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, Name: 1-(Phenylsulfinyl)piperidine.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Karicherla, Venumanikanta published the artcileA Simple and Commercially Viable Process for Improved Yields of Metopimazine, a Dopamine D₂-Receptor Antagonist, Category: piperidines, the publication is Organic Process Research & Development (2017), 21(5), 720-731, database is CAplus.

An efficient, practical, and com. viable manufacturing process was developed with ≥99.7% purity and 31% overall yield (including four chem. reactions and one recrystallization) for an active pharmaceutical ingredient, called Metopimazine I, an antiemetic drug used to prevent emesis during chemotherapy. The development of two in situ, one-pot methods in the present synthetic route helped to improve the overall yield of I (31%) compared with earlier reports (<15%). For the first time, characterization data of API I, intermediates, and also possible impurities are presented. The key process issues and challenges were addressed effectively and achieved successfully.

Organic Process Research & Development published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, Category: piperidines.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Yeo, Jet published the artcileLiquid phase peptide synthesis via one-pot nanostar sieving (PEPSTAR), Computed Properties of 35661-58-6, the publication is Angewandte Chemie, International Edition (2021), 60(14), 7786-7795, database is CAplus and MEDLINE.

Herein, a one-pot liquid phase peptide synthesis featuring iterative addition of amino acids to a “nanostar” support, with organic solvent nanofiltration (OSN) for isolation of the growing peptide after each synthesis cycle is reported. A cycle consists of coupling, Fmoc (Fmoc = 9-fluorenylmethoxycarbonyl) removal, then sieving out of the reaction byproducts via nanofiltration in a reactor-separator, or synthesizer apparatus where no phase or material transfers are required between cycles. The three-armed and monodisperse nanostar facilitates both efficient nanofiltration and real-time reaction monitoring of each process cycle. This enabled the synthesis of peptides more efficiently while retaining the full benefits of liquid phase synthesis. PEPSTAR was validated initially with the synthesis of enkephalin-like model penta- and decapeptides, then octreotate amide and finally octreotate. The crude purities compared favorably to vendor produced samples from solid phase synthesis.

Angewandte Chemie, International Edition published new progress about 35661-58-6. 35661-58-6 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-((9H-Fluoren-9-yl)methyl)piperidine, and the molecular formula is C15H19BO2, Computed Properties of 35661-58-6.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Crich, David published the artcileOn the Use of 3,5-O-Benzylidene and 3,5-O-(Di-tert-butylsilylene)-2-O-benzylarabinothiofuranosides and Their Sulfoxides as Glycosyl Donors for the Synthesis of β-Arabinofuranosides: Importance of the Activation Method, Category: piperidines, the publication is Journal of Organic Chemistry (2007), 72(5), 1553-1565, database is CAplus and MEDLINE.

A 2-O-benzyl-3,5-O-benzylidene-α-D-thioarabinofuranoside was obtained by reaction of the corresponding diol with α,α-dibromotoluene under basic conditions. On activation with 1-benzenesulfinyl piperidine, or di-Ph sulfoxide, and trifluoromethanesulfonic anhydride in dichloromethane at -55 °C, reaction with glycosyl acceptors affords anomeric mixtures with little or no selectivity. The analogous 2-O-benzyl-3,5-O-(di-tert-butylsilylene)-α-D-thioarabinofuranoside also showed no significant selectivity under the 1-benzenesulfinyl piperidine or di-Ph sulfoxide conditions. With N-iodosuccinimide and silver trifluoromethanesulfonate the silylene acetal showed moderate to high β-selectivity, independent of the configuration of the starting thioglycoside. High β-selectivity was also obtained with a 2-O-benzyl-3,5-O-(di-tert-butylsilylene)-α-arabinofuranosyl sulfoxide donor on activation with trifluoromethanesulfonic anhydride. The high β-selectivities obtained by the N-iodosuccinimide/silver trifluoromethanesulfonate and sulfoxide methods are consistent with a common intermediate, most likely to be the oxacarbenium ion. The poor selectivity observed on activation of the thioglycosides with the 1-benzenesulfinyl piperidine, or di-Ph sulfoxide, and trifluoromethanesulfonic anhydride methods appears to be the result of the formation of a complex mixture of glycosyl donors, as determined by low-temperature NMR work.

Journal of Organic Chemistry published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, Category: piperidines.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Fujimoto, James M. published the artcileBarbiturate metabolism as affected by certain agents acting on the liver, Name: 1-Ethylpiperidin-3-ol, the publication is Journal of Pharmacology and Experimental Therapeutics (1960), 139-43, database is CAplus and MEDLINE.

cf. Federation Proc. 17, 369(1958). N-Ethyl-3-piperidyl diphenylacetate (Dactil, JB-305) and benzilate (JB-371), N-methyl-3-piperidyl diphenylcarbamate (JB-371) (I), and β-phenylisopropylhydrazine (Catron, JB-516) (II) prolonged the sleeping time for certain barbiturates in mice, the effect varying with the particular barbiturate selected. Studies employing the whole-body concentration of hexobarbital, isolated rat liver perfusions, and measurements of bromsulfalein-retention point to effects of the prolonging agents on drug metabolites as a major factor in explaining the observed effects. In comparing the inhibitory spectrum of activity of these agents on drug metabolism I was found relatively most specific and II least specific.

Journal of Pharmacology and Experimental Therapeutics published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C7H15NO, Name: 1-Ethylpiperidin-3-ol.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Crich, David published the artcileOn the nitrile effect in L-rhamnopyranosylation, Safety of 1-(Phenylsulfinyl)piperidine, the publication is Carbohydrate Research (2006), 341(10), 1467-1475, database is CAplus and MEDLINE.

It is shown that the use of 5% acetonitrile or propionitrile in dichloromethane functions to increase the β-selectivity of a number of L-rhamnopyranosylation reactions conducted by the thioglycoside method with activation by the 1-benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride couple. The use of more significant quantities of acetonitrile or propionitrile results in the formation of complex reaction mixtures containing little coupled product, but from which Ritter-type products can be isolated.

Carbohydrate Research published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, Safety of 1-(Phenylsulfinyl)piperidine.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Koltun, Dmitry O. published the artcileNovel, potent, selective, and metabolically stable stearoyl-CoA desaturase (SCD) inhibitors, Recommanded Product: 4-(2-Chlorophenoxy)-N-(3-(methylcarbamoyl)phenyl)piperidine-1-carboxamide, the publication is Bioorganic & Medicinal Chemistry Letters (2009), 19(7), 2048-2052, database is CAplus and MEDLINE.

We identified a series of structurally novel SCD (Δ9 desaturase) inhibitors via high-throughput screening and follow-up SAR studies. Modification of the central bicyclic scaffold has proven key to our potency optimization effort. The most potent analog (8g) had IC₅₀ value of 50 pM in a HEPG2 SCD assay and has been shown to be metabolically stable and selective against Δ5 and Δ6 desaturases.

Bioorganic & Medicinal Chemistry Letters published new progress about 1032229-33-6. 1032229-33-6 belongs to piperidines, auxiliary class Metabolic Enzyme,SCD, name is 4-(2-Chlorophenoxy)-N-(3-(methylcarbamoyl)phenyl)piperidine-1-carboxamide, and the molecular formula is C20H22ClN3O3, Recommanded Product: 4-(2-Chlorophenoxy)-N-(3-(methylcarbamoyl)phenyl)piperidine-1-carboxamide.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Yonekuta, Yasunori published the artcileStructural implication of oxoammonium cations for reversible organic one-electron redox reaction to nitroxide radicals, Related Products of piperidines, the publication is Chemistry Letters (2007), 36(7), 866-867, database is CAplus.

Structures and electrochem. behaviors of nitroxide radicals reveal that their rapid and reversible redox reactions are based not only on their chem. stability but also on the increased sp² character of nitrogens which is intermediate between the purely sp² and sp³ nitrogens in oxoammonium cations and amines, resp.

Chemistry Letters published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C2H4ClNO, Related Products of piperidines.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Kelly, Christopher B. published the artcileOxidative cleavage of allyl ethers by an oxoammonium salt, Recommanded Product: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Organic & Biomolecular Chemistry (2015), 13(14), 4255-4259, database is CAplus and MEDLINE.

A method to oxidatively cleave allyl ethers to their corresponding aldehydes mediated by an oxoammonium salt is described. Using a biphasic solvent system and mild heating, the cleavage proceeds readily, furnishing a variety of α,β-unsaturated aldehydes and ketones. E.g, oxidative cleavage of allyl ether (I) in presence of oxoammonium salt (II) gave 79% α,β-unsaturated aldehyde (III).

Organic & Biomolecular Chemistry published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C11H21BF4N2O2, Recommanded Product: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem