Day: December 1, 2022

Yu, V. K. published the artcileEsters of 1-(alkoxyalkyl)-4-piperidinols, SDS of cas: 512778-95-9, the publication is Izvestiya Ministerstva Obrazovaniya i Nauki Respubliki Kazakhstan, Natsional’noi Akademii Nauk Respubliki Kazakhstan, Seriya Khimicheskaya (2002), 70-76, database is CAplus.

4-Piperidinols I (n = 2, R = Me, Et; n = 3, R = Bu, decyl) were prepared by NaBH₄ reduction of the 4-piperidinones. I were esterified with acid chlorides and anhydrides to give the acetates, propanoates, and benzoates, all isolated as the hydrochlorides. The benzoate hydrochlorides exhibited higher local anesthetic activity than lidocaine.

Izvestiya Ministerstva Obrazovaniya i Nauki Respubliki Kazakhstan, Natsional’noi Akademii Nauk Respubliki Kazakhstan, Seriya Khimicheskaya published new progress about 512778-95-9. 512778-95-9 belongs to piperidines, auxiliary class Piperidine,Alcohol,Ether, name is 1-(2-Methoxyethyl)piperidin-4-ol, and the molecular formula is C12H10O4S, SDS of cas: 512778-95-9.

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

Tarumoto, Yusuke published the artcileChemical inhibition of SIK3 as a therapeutic strategy in acute myeloid leukemia, Product Details of C32H34ClN7O3, the publication is Ketsueki Naika (2020), 81(4), 529-534, database is CAplus.

A review. Acute myeloid leukemia AML, a type of hematopoietic aneurysm, is caused by an excessive increase in undifferentiated bone marrow cells. These results suggest that SIK drugs can selectively suppress AML proliferation, indicating that SIK blockade is a candidate for an effective AML treatment strategy. Results show chem. inhibition of SIK3 as therapeutic strategy in acute myeloid leukemia.

Ketsueki Naika published new progress about 1936529-65-5. 1936529-65-5 belongs to piperidines, auxiliary class Immunology/Inflammation,SIK, name is 3-(2-Chloro-6-methylphenyl)-7-((2-methoxy-4-(1-methylpiperidin-4-yl)phenyl)amino)-1-(5-methoxypyridin-2-yl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one, and the molecular formula is C2H2N3NaS, Product Details of C32H34ClN7O3.

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

Sklavounos, Constantine published the artcileD-α-Aminoadipic acid from cephalosporin C, Computed Properties of 72002-30-3, the publication is Organic Preparations and Procedures International (1984), 16(3-4), 165-9, database is CAplus.

The title compound (I) ([α]_D²⁵ = -25.7°, 2% 6N HCl) was prepared by deacylating cephalosporin C via the imino chloride and imino ether to give Me D-α-aminoadipate which was converted to lactam by treatment of base, crystallized, and hydrolyzed to I.

Organic Preparations and Procedures International published new progress about 72002-30-3. 72002-30-3 belongs to piperidines, auxiliary class Piperidine,Chiral,Carboxylic acid,Amide, name is (R)-6-Oxopiperidine-2-carboxylic acid, and the molecular formula is C11H8O3, Computed Properties of 72002-30-3.

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

Reitsema, Robert H. published the artcileNovel rearrangement of a piperidine ring, Application In Synthesis of 13444-24-1, the publication is Journal of the American Chemical Society (1949), 2041-3, database is CAplus.

cf. C.A. 43, 6206i. 1-Ethyl-3-chloropiperidine-HCl (I) (18.4 g.) and 21.4 g. PhCH₂NH₂ in 20 cc. H₂O, heated 48 hrs. at 65-75°, give 73.4% 1-ethyl-2-(benzylaminomethyl)pyrrolidine (II), b₁ 134° (dipicrate, m. 190-1°). 1-Methyl-3-chloropiperidine yields 42% of the 1-Me homolog of II, b_0.2-0.3 110-12° (dipicrate, m. 172-3°). II (2.18 g.) in 50 cc. absolute EtOH, shaken overnight with 2 g. Pd-C (but not with Pt oxide) at 50°, gives 1-ethyl-2-(aminomethyl)pyrrolidine (III), whose dipicrate m. 177-8.5°; III results also from I and alc. NH₃ (20 days at room temperature). I (16 g.), 30.2 g. 8-amino-6-methoxyquinoline, and 25 cc. H₂O, heated 20 hrs. at 60-70° and 2 hrs. at 110°, give 9.1 g. 6-methoxy-8-(1-ethyl-2-pyrrolidylmethylamino)quinoline (IV), b_0.2 186-90°, whose di-HCl salt m. 214-16°, and dipicrate m. 202.5-3.5°. 1-Ethyl-3-piperidone, reduced in MeOH over Raney Ni at 125° and 2270 lb., gives 1-ethyl-3-hydroxypiperidine, whose benzoate-HCl m. 197-8°. IV is less effective for clinical use than many of the new antimalarials.

Journal of the American Chemical Society 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, Application In Synthesis of 13444-24-1.

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

Paul, Raymond published the artcileDerivatives of 3-hydroxypiperidine, Recommanded Product: 1-Ethylpiperidin-3-ol, the publication is Compt. rend. (1945), 221(No. 15), 412-14, database is CAplus.

1,2-Epoxy-5-chloropentane (I) reacts with amines in most cases to form piperidine derivatives I and 1 mol. NHEt₂ at 100° form a colorless solid, apparently the 1-ethyl-3-hydroxypiperidine-EtCl (II). II warmed with concentrated KOH gives C₂H₄ and 1-ethyl-3-hydroxypiperidine (III), b₂₁ 97-98°, d₁₅²³ 0.966, n_D²³ 1.47427 (77% yield based on I). The intermediate 1-diethylamino-5-chloropentane is not isolated. N,N-Diethyltetrahydrofurfurylamine reacts with dry HBr to form a water-soluble product, which reacts with NH₃ to form the ethobromide (IV) of III. IV warmed with concentrated KOH gave C₂H₄ and 74% of III. I and EtNH₂ at 100° form a product which reacts in hot KOH solution to give 74% of III. BzCl and III form the HCl salt of the benzoate ester, colorless needles, m. 204° and possessing marked anesthetic properties. III and excess concentrated HCl at 150° or III and 1 mol. SOCl₂ at 100-120° give 1-ethyl-3-chloropiperidine (V), colorless liquid of moldy odor, b₂₀ 75°, d₁₅^19.5 0.996, n_D^19.5 1.46807. Picrate of V m. 156-7°; methiodide, m. about 210 °. Aniline and 1 mol. I give at 120° 1-phenyl-3-hydroxypiperidine, colorless liquid, b₁₆ 176°, d₁₆¹⁵ 1.099, n_D¹⁵ 1.57856, and not N-phenyltetrahydrofurfurylamine (VI), b₁₀ 155-6°, d₁₆¹¹ 1.075, n_D¹¹ 1.56456, which was obtained by the action of aniline and tetrahydrofurfuryl chloride (VII) at 150°. The piperidine ring is not always formed, as shown by the action of PhNHEt on I for 12 h. at 125°. N-Tetrahydrofurfuryl-N-ethylaniline (VIII), b₂₀ 176-7°, d₁₆²² 1.052, n_D²² 1.55962, was formed. VIII was also obtained by direct action of PhNHEt on VII.

Compt. rend. 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, Recommanded Product: 1-Ethylpiperidin-3-ol.

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

Mitchell, Robin E. published the artcileSynthesis of amino acid conjugates to 2-imino-3-methylene-5-carboxypyrrolidine and 2-imino-3-methylene-6-carboxypiperidine, Recommanded Product: (R)-6-Oxopiperidine-2-carboxylic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(6), 1910-1912, database is CAplus and MEDLINE.

The four stereomers of 2-imino-3-methylene-5-(carboxy-L-valyl)pyrrolidine, a bacterial metabolite that is inhibitory to the fire blight bacterium Erwinia amylovora, were synthesized and compared for antibacterial activity. Several alternative amino acid conjugates with L,L-stereochem. were also prepared, and the synthesis was extended to 3-methylenepiperidine-6-L-carboxylic acid and a selection of 2-imino-3-methylenepiperidine-6-L-carboxy-L-amino acid conjugates. All synthetic amino acid conjugates (L,L-stereomers) were inhibitory to the growth of E. amylovora. The likely participation of the conjugated iminomethylene moiety as a Michael acceptor is implicated.

Bioorganic & Medicinal Chemistry Letters published new progress about 72002-30-3. 72002-30-3 belongs to piperidines, auxiliary class Piperidine,Chiral,Carboxylic acid,Amide, name is (R)-6-Oxopiperidine-2-carboxylic acid, and the molecular formula is C6H9NO3, Recommanded Product: (R)-6-Oxopiperidine-2-carboxylic acid.

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

Manap, Sevda published the artcileSynthesis and in vitro antioxidant and antimicrobial activities of novel 3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones, and their N-acetyl, N-Mannich base derivatives, COA of Formula: C6H12N2O, the publication is Journal of the Iranian Chemical Society (2022), 19(4), 1347-1368, database is CAplus.

The reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones I (R = Me, Ph, Bn, etc.) with 3-methoxy-4-(2-furylcarbonyloxy)-benzaldehyde formed 3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones II (R¹ = H). Moreover, their five N-acetyl derivatives II (R¹ = acetyl) were synthesized. Besides, compounds II (R¹ = morpholin-4-yl-methyl)/II (R¹ = N-methylpiperazinyl)/II (R¹ = (4-carbamoylpiperidin-1-yl)methyl)/III were obtained by Mannich reaction between compounds II (R¹ = H) and morpholine/N-methylpiperazine/piperidine-4-carboxyamide/piperazine in the presence of formaldehyde. Also, these compounds were evaluated for their in vitro antioxidant activity. Furthermore, in vitro antibacterial activity of the compounds was screened against six bacteria.

Journal of the Iranian Chemical Society 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, COA of Formula: C6H12N2O.

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

Deguchi, Yoshio published the artcilePiperidine derivatives, Computed Properties of 14613-37-7, the publication is Iyaku Shigen Kenkyusho Nempo (1956), 17-22, database is CAplus.

Dialkylureido-N-methylpiperidines and dialkylureidomethyl-N-methylpiperidines were prepared Pyridine-3-carboxylic acid amide (10 g.) is refluxed with 17.5 g. MeI and 30 cc. MeOH for 5 hrs., evaporated, the residue is dissolved in 30 cc. H₂O, warmed with freshly prepared AgCl (prepared from 20 g. AgNO₃ and 7 g. NaCl) for 3 hrs., and filtered. The filtrate is decolorized with active C and then catalytically reduced with 0.1 g. PtO₂ to give 85% N-methylpiperidine-3-carboxamide (I); hydrochloride m. 232° (alc.). Similarly was prepared N-methylpiperidine-4-carboxamide; hydrochloride, hygroscopic. A mixture of 7 g. I and 7 g. P₂O₅ is heated at 160-180° for 3 hrs., cooled, dissolved in 50 cc. H₂O with warming, neutralized with K₂CO₃, salted out, and the separated oil extracted with AcOEt to give 80% 3-cyano-N-methylpiperidine (II), b₂₀ 95-6°. Similarly was prepared 4-cyano-N-methylpiperidine, b₂₁ 97°. Into a cooled mixture of 1.3 g. LiAlH₄ and 150 cc. Et₂O is dropped a solution of 5.0 g. II in 50 cc. Et₂O during 90 min., the mixture stirred 1 hr., refluxed 30 min., 15 cc. H₂O added to decompose excess LiAlH₄, and filtered. The filtrate is dried with KOH, evaporated, and distilled in vacuo to give 90% 3-aminomethyl-N-methylpiperidine (III), b₂₀ 81-2°; dipicrate m. 231° (decomposition). Similarly was prepared 4-aminomethyl-N-methylpiperidine (IV), b₂₀ 80-1°; dipicrate m. 236° (decomposition). To a mixture of 32 g. KOH, 6.4 g. Br, and 400 cc. H₂O is dropped an aqueous solution of 5.7 g. I under ice cooling, then warmed at 70° for 1 hr., alkalized with KOH, distilled with steam, and the distilled solution treated with diluted HCl, concentrated in vacuo, alkalized with KOH, extracted with Et₂O, and the extract evaporated and distilled in vacuo to give 65% 3-amino-N-methylpiperidine (V), b₄₃ 74-5°; dipicrate m. 227° (decomposition). Similarly was prepared 4-amino-N-methyl-piperidine (VI), b₃₅ 70-1°; dipicrate m. 263° (decomposition). A mixture of 0.6 mole Me₂NH and 200 cc. PhMe is dropped into 50% phosgene-PhMe, refluxed 1 hr., and distilled in vacuo to give 40% dimethylcarbamoyl chloride (VII), b_55-60 85-8°. Similarly was prepared diethylcarbamoyl chloride (VIII), b_17-20 80°. A mixture of 2 moles III and 1 mole VII in Et₂O is kept at room temperature 1.5 hrs., refluxed 10 min., cooled, and filtered. The filtrate is evaporated and chromatographed using alumina to give 3-dimethylureidomethyl-N-methyl-piperidine, needles (petr.-ether), m. 66-9° (hygroscopic). Similarly were prepared following IX (starting materials, position of substituent, n, R, appearance, and m.p. given): III and VIII, 3, 1, Et, sirupy, -; IV and VII, 4, 1, Me, needles (hygroscopic), 40-4° (hydrochloride m. 230°); IV and VIII, 4, 1, Et, columns, 66-8°; V and VIII, 3, 0, Me, needles, 110-12°; V and VIII, 3, 1, Et, sirupy, (picrolonate m. 195-7°); VI and VII, 4, 0, Me, flakes, 138-9°; VI and VIII, 4, 0, Et, needles, 89-90°.

Iyaku Shigen Kenkyusho Nempo published new progress about 14613-37-7. 14613-37-7 belongs to piperidines, auxiliary class Piperidine,Amine, name is (1-Methylpiperidin-3-yl)methanamine, and the molecular formula is C7H16N2, Computed Properties of 14613-37-7.

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

Correale, Jorge published the artcileBruton’s tyrosine kinase inhibitors as potential therapies for multiple sclerosis, Computed Properties of 1971920-73-6, the publication is Lancet Neurology (2021), 20(9), 689-691, database is CAplus and MEDLINE.

A review. Over the past 30 years increasing numbers of mols. have been developed for treatment of multiple sclerosis. Bruton’s tyrosine kinase is a cytoplasmic tyrosine kinase expressed by B cells and myeloid cells. Both B cells and myeloid cells (particularly microglia) are important drivers of multiple sclerosis, suggesting that inhibitors of Bruton’s tyrosine kinase, such as the irreversible inhibitors evobrutinib, tolebrutininb, and orelabrutinib, and the reversible inhibitors fenebrutinib and BIIB091, might provide therapeutic benefits for patients. Bruton’s tyrosine kinase inhibitors could provide attractive therapeutic benefits for patients with multiple sclerosis, with potential advantages over monoclonal antibodies because they might be less likely to trigger antibody responses, allergic reactions,or neutralisation of their therapeutic actions. Addnl., these inhibitors, as small mols., might be able to access the CNS and inhibit microglial activation. However, whether Bruton’s tyrosine kinase inhibitors will be more efficacious than monoclonal antibodies remains to be established.

Lancet Neurology published new progress about 1971920-73-6. 1971920-73-6 belongs to piperidines, auxiliary class Other Aliphatic Heterocyclic,Piperidine,Alkenyl,Amine,Benzene,Ether,Inhibitor,Inhibitor, name is (R)-1-(1-Acryloylpiperidin-3-yl)-4-amino-3-(4-phenoxyphenyl)-1H-imidazo[4,5-c]pyridin-2(3H)-one, and the molecular formula is C26H25N5O3, Computed Properties of 1971920-73-6.

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

Campbell, A. F. published the artcileThe separation of m-and p-cresols from coal-tar crude carbolic acid, Safety of 1-(Phenylsulfinyl)piperidine, the publication is Journal of Industrial and Engineering Chemistry (Washington, D. C.) (1922), 732-7, database is CAplus.

The fractions obtained by the distillation of the crude product consist principally of (1) PHOH, (2) o-cresol, (3) m- and p-cresols and (4) xylenols and other complex phenols. Fractionation of (3) gives a PhOH-free product containing 59-60% m-cresol. The sulfonation of this with 96%, H₂SO₄ at 40 for 6 hrs., and subsequent treatment with H₂O gives an extract (A) of non-sulfonated cresols and an aqueous solution (B) of monosulfonates containing 78-80% of the m-compound B is converted into the NH₄ salts through the Ba salts and on fractional crystallization yields a product containing 98-100% m-cresol. The further sulfonation of A with 96% H₂SO₄ gives a non-sulfonated product (C) containing about 80% p-cresol and a sulfonated product (D) containing about 58% m-cresol, which is further sulfonated for obtaining the m-compound C may be treated so that a product containing 89% p-cresol is obtained.

Journal of Industrial and Engineering Chemistry (Washington, D. C.) 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