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, nD23 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°, d1519.5 0.996, nD19.5 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, nD15 1.57856, and not N-phenyltetrahydrofurfurylamine (VI), b10 155-6°, d1611 1.075, nD11 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, nD22 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