Shapiro, Seymour L. published the artcileAntihypertensive agents. III. Dialkylaminoalkoxypiperidines and related compounds, Computed Properties of 13444-24-1, the publication is Journal of Organic Chemistry (1960), 291-3, database is CAplus.
cf. CA 52, 18396h; 54, 6775c. Reductive alkylation of N-alkyl-3-piperidinols with HCHO and AcH, resp., gave 73% N-methyl-3-piperidinol, b40 103-4°, and 51% N-ethyl-3-piperidinol, b40 126-8°. 3-Pyridinemethanol (66.8 g.) in 500 ml. MeCN cooled to -5° during the addition of 95 g. MeBr, and the mixture stored 20 hrs. at 20° gave 89 g. 3-(hydroxymethyl)-1-methylpyridinium bromide, m. 92-4° (iso-PrOH-isopropyl ether). 1-Hydroxymethyl-3-piperidinomethanol-HBr, prepared in 70% yield, m. 113-15° (alc.-MeCOEt). 4-Pyridinemethanol (89.1 g.) and 133 g. EtBr in 800 ml. MeCN refluxed 24 hrs. gave 170 g. crude 4-hydroxymethyl-1-ethylpyridinium bromide (I). Crude I hydrogenated directly and converted into the base with 40% NaOH, and the mixture salted, extracted with Et2O, and dried gave 31% 4-hydroxymethyl-1-ethylpiperidine. 2-Pyridinemethanol (22 g.) and 40.7 g. PhCH2CH2Br in 250 ml. MeCN refluxed 22 hrs. gave 19 g. 2-hydroxymethyl-1-phenethylpyridinium bromide (II), m. 158-9° (alc.). II (14 g.) in 250 ml. alc. and 1.3 g. 5% Rh on C on complete hydrogenation after 3 hrs. gave 10 g. 1-phenethyl-2-piperidinemethanol-HBr, m. 157-8°. NaH (3.1 g.) in 50 ml. PhMe treated during 40 min. with 15.4 g. 1-ethyl-3-piperidinol in 50 ml. PhMe, stirred 2 hrs. at 20°, then refluxed 2 hrs., treated over 1 hr. with 38.4 g. Me2N(CH2)3Cl.HCl in H2O, made basic, extracted with PhMe, and the mixture refluxed 6 hrs. gave 9.8 g. 3-(3-dimethylaminopropoxy)-1-ethylpiperidine (III). Addition of 3.2 g. III in 10 ml. MeCN to 4.7 g. MeI in 15 ml. MeCN after 20 hrs. gave 4.7 g. 3-(3-dimethylaminopropoxy)-1-ethyl-1-methylpiperidinium iodide-MeI. The following (dialkylaminoalkoxy)alkylpiperidines were thus obtained (1-substituent, 2nd substituent, % yield, m.p. or b.p./mm. given): Me, 3-O-(CH2)2NMe2, 11, 100-3°/9; Me, 3-O(CH2)2NMe2 (di-MeI salt), 60, 294-7°; Et, 3-O(CH2)2NMe2, 17, 102-6°/8; Me, 3-O(CH2)3NMe2, 50, 142-4°/35; Me, 3-O(CH2)3-NMe2 (di-MeI salt), 85, 214-16°; Me, 3-O(CH2)3NMe2, (di-EtI salt), 71, 171-4°; Et, 3-O(CH2)3NMe2, 38, 116-18°/6; Et, 3-O(CH2)3NMe2 (di-MeI salt), 52, 197-200°; Me, 3-CH2O(CH2)2NEt2, 10, 113°/2; Et, 4-CH2O(CH2)2-NEt2, 40,106°/0.9; PhCH2CH2, 2-CH2O(CH2)2NEt2, 4, 120-4°/0.08.
Journal of Organic Chemistry 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 C9H6ClNS, Computed Properties of 13444-24-1.
Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem