Category: 13444-24-1

Abood, L. G. published the artcileA new class of psychotogenic substances, Computed Properties of 13444-24-1, the publication is Mol. Mental Health, Papers Sci. Congrs. Brain Research Foundation; New York and Chicago (1959), 69-76, database is CAplus.

Piperidyl benzilate derivatives of formula CH₂(CH₂)₂NACH₂CHOCOCBRC₆H₅ were tested on humans for psychotogenic effects. With A, B, and R, resp., Et, OH, cyclohexyl; Et, OH, cyclopentyl; Me, OH, Ph; Me, OH, 2-thienyl; Et, OH, Ph; Et, OH, Pr; Et, H, Ph; 2Me, OH, Ph; and Et and Me, OH, Ph. With R as some cycloalkyl group the psychotogenic potency is greater than with phenyl substitution. If R is a thienyl group, the duration of the response is considerably less, although the psychotogenic effectiveness is about the same. The 4-piperidine linked isomers are less active than the 3 isomers. If A is Me, the maximum potency is obtained; with higher aliphatic chains the potency decreases. Replacement of H in the benzilic acid moiety by OH leads to a disappearance of potency. The same effect occurs if the piperidine N is made quaternary. No correlation between psychotogenic and anticholinergic potency was found.

Mol. Mental Health, Papers Sci. Congrs. Brain Research Foundation; New York and Chicago 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, Computed Properties of 13444-24-1.

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

Abood, L. G. published the artcileStructure-activity relationships of 3-piperidyl benzilates with psychotogenic properties, Related Products of piperidines, the publication is Archives Internationales de Pharmacodynamie et de Therapie (1959), 186-200, database is CAplus.

Correlation of pharmacol. and psychotogenic properties of compounds of structure CH₂.CH₂.CH₂NA.CH₂.CHOCOC(Ph)(B)(R) was attempted. In addition to auditory and visual hallucinations, mood changes, disorientation, hypochondriacal and paranoid delusions, and partial loss of contact were observed on administration of such compounds The most effective compound was N-methyl-3-piperidyl phenylcyclohexyl glycolate (I). Other materials studied included (given in order are A, B, and R): Me, OH, cyclohexyl (II); Et, OH, II; Et, OH, cyclopentyl; Me, OH, Ph; Me, OH, 2-thienyl; Et, OH, Ph; CH₂CH₂NMe₂, OH, Ph; 1,2,2,6,6-pentamethyl (3-piperidyl isomer), OH, Ph; Me, OH, Ph; Et, OH, Pr; H, OH, Ph; Et, H, Ph; (CH₃)₂, OH, Ph; and (C₂H₅)CH₃, OH, Ph. These compounds were potent anticholinergic agents, the best being the 2-thienyl compound Most compounds were antihistamines. Physostigmine counteracted anticholinergic effects but potentiated muscular ones. These compounds effectively blocked mydriasis, tachycardia, and hyperemia. Substitution of H for OH abolishes psychotogenic properties as does quaternization of the piperidyl ring. Replacement of Ph with II in compounds containing N-Me or N-Et enhances psychotogenic effects. Substitution of 2-thienyl for Ph diminishes reaction duration but increases anticholinergic and antihistaminic potencies. The psychotogenic properties do not correlate with toxicity, antispasmodic potency, of mydriasis.

Archives Internationales de Pharmacodynamie et de Therapie 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, Related Products of piperidines.

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

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

Abood, L. G. published the artcilePossible role of brain mitochondria in psychopharmacology, Application In Synthesis of 13444-24-1, the publication is Journal of Neuropsychiatry (1959), 92-5, database is CAplus.

cf. CA 53, 22487b. Experiments were performed on rat-brain mitochondria to determine the presence of cholinergic receptor sites. It was observed that the distribution of tritiated N-ethyl-3-piperidyl benzilate (JB-318) (I) was similar to that of acetylcholine in the cellular fractions of rat brain. The largest concentration was found in the mitochondria. It was concluded that the cholinergic receptor sites were in this fraction or granules associated with this fraction. The inhibition of a number of drugs upon the binding of I to mitochondria was chlorpromazine 80, 3-piperidyl benzilate (JB-305) and N,N’-piperazinodiethyl dibenzilate 50, hydroxyzine 44, and dinitrophenol 20%. It was suggested that if the receptor sites are confined to cytoplasmic particles, then the phenothiazine types of tranquilizers and the psycho-mimetic agents act at the mitochondrial level of the cell.

Journal of Neuropsychiatry 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

Fuson, Reynold C. published the artcileRing enlargement by rearrangement of the 1,2-aminochloroalkyl group; rearrangement of 1-ethyl-2-(chloromethyl)pyrrolidine to 1-ethyl-3-chloropiperidine, HPLC of Formula: 13444-24-1, the publication is Journal of the American Chemical Society (1948), 2760-2, database is CAplus.

Reduction of 1,2-dicarbethoxypyrrole over Raney Ni in dry MeOH at 70°/1500 lb. gives 95% 1,2-dicarbethoxypyrrolidine; further reduction over Cu chromite in EtOH at 250°/100 atm. gives 31% 1-ethyl-2-hydroxypyrrolidine (I); the HCl salt and benzoate-HCl are oils; benzoate picrate, m. 170.5-1.5°. Diethyl(tetrahydrofurfuryl)amine yields 43% 1-ethyl-3-hydroxypiperidine, which forms a HCl salt (II), m. 157-8°, and a benzoate picrate, yellow, m. 181.5-2.5°. I (4 g.) in 25 ml. CHCl₃ at 0°, treated with HCl to form the HCl salt and then with 4.8 g. SOCl₂ in CHCl₃, and the mixture stirred 30 min. at room temperature and refluxed 1 hr., gives 56% 1-ethyl-2-(chloromethyl)pyrrolidine-HCl (III), m. 165-70° (heated 20°/min.), solidifies, and m. 153.5-4°; slowly heated, III contracts at 165° and m. 193.5-4°; picrate, m. 128.5-9.5°. The Me₂CO used to wash the crude III yields 1.4 g. 1-methyl-2-(chloromethyl)pyrrolidine picrate (?) (IV), m. 163.5-4.5°; it is possible that I contained some 1-ethyl-2-(hydroxymethyl)pyrrolidine. II (5 g.) and 3.7 g. SOCl₂ in 50 ml. PhMe, refluxed 3 hrs., give 87% 1-ethyl-3-chloropiperidine (V) as the HCl salt (VI), m. 193.5-4°; a mixture of III and VI also m. 193.5-4°. The base from III appears to undergo rearrangement to V as rapidly as it is liberated, an ethylenimonium ion probably being an intermediate. The base (V) from VI does not undergo rearrangement on liberation. The attempt to prepare 1-methyl-3-chloropiperidine from IV was inconclusive.

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, HPLC of Formula: 13444-24-1.

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

Schultz, Otto E. published the artcileMechanism of local anesthetic action. 1. Receptor problem, SDS of cas: 13444-24-1, the publication is Pharmazie (1970), 25(8), 472-80, database is CAplus and MEDLINE.

Furfuryl alc. was treated 1 hr at -5° with PBr3 and the product treated with MeNH2 and alc. NaI 72 hr at 100-20° to give I. Treatment of I with HBr-HOAc gave a ring-opened product which was cyclized with KOH to give 63% II. Similarly prepared were 10 other compounds including III, IV, V, VI, and VII. The local anesthetic activity of these compounds vs. procaine-HCl (III) was determined III had 80% of the VIII activity. The mechanism of local anesthetic activity is discussed.

Pharmazie 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 C8H5F3O2S, SDS of cas: 13444-24-1.

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

Mahssin, Zakariya Y. published the artcileHydrothermal liquefaction bioproduct of food waste conversion as an alternative composite of asphalt binder, Related Products of piperidines, the publication is Journal of Cleaner Production (2021), 125422, database is CAplus.

Considerable environmental concern regarding increased food wastage caused by population and economic growth has been raised worldwide. The verification of food waste recycling product for engineering purposes is also vague. This work evaluates a liquefied bio-product recovered from the hydrothermal liquefaction of food waste as a potential non-petroleum-based binder in asphalt pavement. Various parameters were evaluated to optimize the liquefaction reaction for the enhancement of the liquefied food waste (LFW) product recovered from the process. The LFW was characterized for chem. compound and used to substitute different portions of conventional asphalt binders 60/70 pen (i.e., 10%, 20%, and 30%) from the total binder weight The conventional and modified asphalt binders were evaluated for storage stability, phys. and chem. properties, thermal decomposition, and functional groups. Thermal degradation affirms the presence of LFW in the modified asphalt, and the low mol. weight concerning high-b.p. compounds were identified. The use of LFW in the asphalt binder produces a modified binder with phys. properties and storage stability that are comparable with those of petroleum-based asphalt, thereby suggesting that the liquefied product obtained from food waste can be used as bio-binder in asphalt pavement.

Journal of Cleaner Production 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, Related Products of piperidines.

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

Chowdhury, Firoz Alam published the artcileCO₂ Capture by Tertiary Amine Absorbents: A Performance Comparison Study, Safety of 1-Ethylpiperidin-3-ol, the publication is Industrial & Engineering Chemistry Research (2013), 52(24), 8323-8331, database is CAplus.

This work assessed CO₂ capture with 24 tertiary amine absorbents (including 3 synthetic amines) with systematic modification of their chem. structures. Aqueous amine solutions (30 % mass fraction) were used to evaluate CO₂ capture performance. Laboratory gas scrubbing, vapor-liquid equilibrium, and reaction calorimetry experiments were conducted to obtain the absorption rate, amount of CO₂ absorbed, cyclic CO₂ capacity, and heat of reaction for each absorbent. Results for were compared with the conventional tertiary absorbent, N-methyldiethanolamine (MDEA). Seven of the studied absorbents performed well with high absorption rates and cyclic capacities. Among these absorbents, some displayed lower heats of reaction than MDEA. Results provided basic guidelines to discover potential tertiary amine-based absorbents which may lead to development of new absorbent systems for CO₂ capture.

Industrial & Engineering Chemistry Research 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, Safety of 1-Ethylpiperidin-3-ol.

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

Rozanska, Xavier published the artcileQuantitative Kinetic Model of CO₂ Absorption in Aqueous Tertiary Amine Solvents, Quality Control of 13444-24-1, the publication is Journal of Chemical Information and Modeling (2021), 61(4), 1814-1824, database is CAplus and MEDLINE.

Aqueous tertiary amine solutions are increasingly used in industrial CO₂ capture operations because they are more energy-efficient than primary or secondary amines and demonstrate higher CO₂ absorption capacity. Yet, tertiary amine solutions have a significant drawback in that they tend to have lower CO₂ absorption rates. To identify tertiary amines that absorb CO₂ faster, it would be efficacious to have a quant. and predictive model of the rate-controlling processes. Despite numerous attempts to date, this goal has been elusive. The present computational approach achieves this goal by focusing on the reaction of CO₂ with OH^– forming HCO₃^–. The performance of the resulting model is demonstrated for a consistent exptl. data set of the absorption rates of CO₂ for 24 different aqueous tertiary amine solvents. The key to the new model’s success is the manner in which the free energy barrier for the reaction of CO₂ with OH^– is evaluated from the differences among the solvation free energies of CO₂, OH^–, and HCO₃^–, while the pK_a of the amines controls the concentration of OH^–. These solvation energies are obtained from mol. dynamics simulations. The exptl. value of the free energy of reaction of CO₂ with pure water is combined with information about measured rates of absorption of CO₂ in an aqueous amine solvent in order to calibrate the absorption rate model. This model achieves a relative accuracy better than 0.1 kJ mol^-1 for the free energies of activation for CO₂ absorption in aqueous amine solutions and 0.07 g L^-1 min^-1 for the absorption rate of CO₂. Such high accuracies are necessary to predict the correct exptl. ranking of CO₂ absorption rates, thus providing a quant. approach of practical interest.

Journal of Chemical Information and Modeling 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, Quality Control of 13444-24-1.

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