Mikhlina, E. E. published the artcileSynthesis of 3- and 4-hydroxypiperidine derivatives, Related Products of piperidines, the publication is Zhurnal Obshchei Khimii (1960), 1885-93, database is CAplus.
cf. CA 54, 22632h. Refluxing 1-ethyl-3-hydroxypiperidine with p-ClC6H4COCl in C6H6 gave 62.5% 1-ethyl-3-(p-chlorobenzoxy)piperidine-HCl, m. 185-7°. Similarly were prepared 68-93% yields of HCl salts of the corresponding: acetate, m. 179-81°; propionate, m. 174-5°; p-nitrobenzoate, m. 175-7°; phenoxyacetate, m. 160-2°; and cinnamate, m. 164-6°. 4-Piperidone-HCl with NaBH4 in EtOH with ice cooling gave in 20 h. 61% 4-hydroxypiperidine, b13 106°. Similarly was prepared 83.5% 1-methyl-4-hydroxypiperidine, b12 94°, and 84.5% 1-ethyl-4-hydroxypiperidine, b5 91°. 1-Ethyl-3-hydroxypiperidine with CH2:CHCN in dioxane-MeOH in the presence of 30% KOH in MeOH gave in 4 h. at 65° 80.2% 1-ethyl-3-(2-cyanoethoxy)piperidine (I), b3 125-6°. Similarly were prepared 80% 1-methyl-4-(2-cyanoethoxy)piperidine, b7 125-6°, n17D 1.4668, and 1-Et analog, b4 122°. I and dry HCl in refluxing EtOH 4 h. gave 66.6% 1-ethyl-3-(2-carbethoxyethoxy)piperidine (II), b3 120-1°, n17D 1.4589, also formed by the use of EtOH-H2SO4 in 18 h. at reflux. Similarly were prepared 48% 1-methyl-4-(2-carbethoxyethoxy)piperidine, b2 102°, n18D 1.4558, and 66% 1-ethyl-4-(2-carbethoxyethoxy)piperidine, b4 113°. II with LiAlH4 in Et2O gave 86.8% 1-ethyl-3-(γ-hydroxypropoxy)piperidine (III), b3 116-18°, n17D 1.4749. Similarly were prepared 76.3% 1-methyl-4-(γ-hydroxypropyl)piperidine, b4 114-16°, n17D 1.4741, and 88% 1-Et analog, b5 125°, n24D 1.4713. III treated with EtOH-HCl, evaporated, and treated with SOCl2 in MePh gave after aqueous treatment 1-ethyl-3-(γ-chloropropoxy)piperidine, which refluxed 6 h. with thiourea in N HCl then heated with aqueous NaOH 0.5 h. gave 71.4% 1-ethyl-3-(γ-mercaptopropoxy)piperidine, b8 132-3°. Similarly was prepared 71% 1-methyl-4-(γ-mercaptopropoxy)piperidine (IV), b0.7 100°, and 57.2% 1-ethyl-4-(γ-mercaptopropoxy)piperidine, b1 110°. III treated with SOCl2 in hot C6H6 3 h. at 65°, evaporated, and made alk. with K2CO3 gave crude 1-ethyl-3-(γ-chloropropoxy)piperidine, which treated with thiourea in aqueous EtOH 6 h. gave 43.2% bis[γ-(1-ethyl-3-piperidyloxy)propyl] sulfide, b0.5 202-7°. Heating 1-methyl-4-(γ-hydroxypropoxy)piperidine with AcCl in C6H6 6 h. gave 94% 1-methyl-4-(γ-acetoxypropoxy)piperidine, b3 111°; methiodide m. 77-9°. IV with BzCl in Et2O gave 91% 1-methyl-4-(γ-benzoylthiopropoxy)piperidine-HCl, m. 129.5-30°. Similarly were prepared the following 1-ethyl-3-(γ-acyloxypropoxy)piperidines (acyl group shown): propionate, b1 125-7°; benzoate, b1 190-2°; p-nitrobenzoate, b1 201-3°; and pyridylcarbonyl, b0.6 177-8°. Also reported was 1-ethyl-3-(γ-acetylthiopropoxy)piperidine, b0.75 135°. The following 1-alkyl-4-[γ-acyloxy(or acylthio)propoxy] piperidines were reported (alkyl and acyl groups shown, resp.): Me, benzoxy, b3 170-1° (HCl salt m. 120°); Me, p-nitrobenzoylthio (HCl salt m. 127-8°); Me, p-chlorobenzoylthio (HCl salt m. 127-31°; Me, acetylthio, b0.5 107-10°; Me, diphenylacetylthio (HCl salt m. 57-7.5°); Et, acetoxy, b0.5 97°; Et, benzoxy, b0.5 155-61°; Et, diphenylacetoxy, b0.7 203-5°; Et, acetylthio (HCl salt m. 68°); Et, benzoylthio (HCl salt m. 124-5°); Et, phenylacetylthio (HCl salt m. 95-7°); Et, diphenylacetylthio (HCl salt m. 103-7°); Bu, benzoylthio (HCl salt m. 115-18°); Bu, acetylthio (HCl salt m. 102-3°). Acrylonitrile with 4-hydroxypiperidine in the presence of KOH in MeOH-dioxane gave 74.5% 4-(2-cyanoethoxy)piperidine, b2 135°, n14D 1.4630, which with HCl-EtOH at reflux gave 65.5% 4-(2-carbethoxyethoxy)piperidine, b4 122°. This in pyridine treated with PrCOCl 4 h. at 65°, the crude product after aqueous treatment neutralized with K2CO3, extracted with C6H6, and reduced with LiAlH4 gave 56% 1-butyl-4-(γ-hydroxypropoxy)piperidine, b0.5 130-2°.
Zhurnal Obshchei Khimii 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