Dahlbom, Richard; Misiorny, Alfons published an article in 1957, the title of the article was Amines related to adrenaline containing nuclear chlorine.Formula: C18H19NO3 And the article contains the following content:
Nuclear substituted amino ketones were prepared from appropriate ω-chloroacetophenones and the desired amines. E.g., the appropriate ω-chloroacetophenone (0.025 mole) and the amine (0.065 mole) were dissolved in toluene (usually 25 ml.) and the mixture kept overnight at room temperature The amine hydrochloride was removed by filtration and the toluene solution washed with water and extracted with 2N HCl. The extract was made alkaline with aqueous Na2CO3 and the precipitated base extracted with Et2O. The extract was dried over Na2SO4 and the amino ketone was then isolated as the hydrochloride by the addition of ethereal HCl and recrystallized These compounds were of the general formula 3,4-R’RC6H3COCH2R”.HCl with R, R’, R”, and m.p. given: Cl, H, piperidino (I), 222-3° (free amine, m. 52-3°); OH, Cl, I, 268-270°; Cl, Cl, I, 249-51°; Cl, H, NHEt, 246-8°; Cl, H, 4-methyl-1-piperazinyl (II), 248-9°; Cl, Cl, II, 252-4°; Cl, H, 4-ethyl-1-piperazinyl, 266-8°; Cl, H, 4-carbethoxy-1-piperazinyl (III), 196-7°; Cl, Cl, III, 212-14° (free amine, m. 108-9°). Most of these amine hydrochlorides m. with decomposition and the yields were 41-87%. The hydrochlorides were converted to the free amino ketones which were dissolved in Et2O and reduced with LiAlH4 to give the following corresponding amino alcohols with R, R’, R”, and m.p. given in that order; Cl, H, I, 68.5-70°; Cl, Cl, I, 89-90°; Cl, H, NHEt, b0.8 190°, m. 87-8°; Cl, H, II, 85-85.5° (hydrochloride, m. 236-7°); Cl, Cl, II, 121-2°. A weak antagonism toward adrenaline and noradrenaline was shown by several of the piperidino compounds in experiments on the blood pressure of cats. The experimental process involved the reaction of N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas: 456-12-2).Formula: C18H19NO3
N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas:456-12-2) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Formula: C18H19NO3
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics