Chaudhury, N. Aditya; Chatterjee, A. published an article in 1959, the title of the article was β-Phenylethanolamines. I. New synthesis of aegeline and papaverine.Electric Literature of 456-12-2 And the article contains the following content:
cf. C.A. 52, 14630i. Substituted benzaldehyde cyanohydrins are reduced to the corresponding amines, condensed with piperonal (I), and converted to the N-Me derivatives Thus, 6 g. p-MeOC6H4CH(OH)CN in 50 cc. Et2O is added dropwise to 4 g. LiAlH4 in 200 cc. Et2O at 0°, the mixture stirred at room temperature 5-6 hrs., refluxed 4-5 hrs., the complex decomposed by addition of 5 cc. H2O, 10 cc. 20% aqueous NaOH, and 15 cc. H2O and refluxed 30 min. The solution is filtered hot, extracted with 150 cc. Et2O and β-hydroxy-β-(p-methoxyphenyl)ethylamine (II) (80%), m. 70° (C6H6-petr. ether), isolated by evaporation of the Et2O. II.HCl m. 173°. Equal moles of I and II are refluxed in 95% EtOH 1 hr. and the solvent evaporated in vacuo to give N-piperonylidene-β-hydroxy-β-(p-methoxyphenyl)ethylamine (III) (90-5%), needles, m. 115-16° (C6H6-petr. ether). III (3 g.) in 100 cc. C6H6 is refluxed with 5 cc. MeI 5-6 hrs., the sticky solid product dissolved in 20-5 cc. hot water and 2-3 cc. concentrated HCl, warmed 1 hr., extracted with Et2O, made alk. with 30% NaOH, and extracted with Et2O and then CHCl3. From the combined extracts on distillation in vacuo is obtained N-methyl-β-hydroxy-β-(p-methoxyphenyl)ethylamine (50 %); HCl salt, needles, m. 101° (Me2CO-EtOAc). From the corresponding cyanohydrins are prepared: β-hydroxy-β-(3,4-dimethoxyphenyl)ethylamine (72%), b4 180-2°; HCl salt (IV), m. 163°; its I derivative m. 129-30°; and N-methyl-β-hydroxy-β(3,4-dimethoxyphenyl)ethylamine (46%), HCl salt m. 143-5° (decomposition); also β-hydroxy-β-(3,4-methylenedioxyphenyl)ethylamine (80%), HCl salt m. 181-2°; its I derivative m. 155-6°; and N-methyl-β-hydroxy-β-(3,4-methylene-dioxyphenyl)ethylamine (50%), HCl salt m. 163-5° (decomposition). Homoveratroyl chloride (3 g.) is added to 2 g. IV in the min. amount of H2O, 1.5 g. KOH added, the mixture stirred vigorously 2 hrs., the yellow mass which separates washed with a little H2O, dissolved in the min. amount EtOH containing a few drops dilute NaOH, and allowed to stand 1 day to give 2 g. homoveratroyloxyhomoveratrylamine (V), m. 127-8° (C6H6). V (2 g.) refluxed in PhMe 5 min. with 10 g. P2O5, the PhMe decanted, the residue dissolved in ice H2O, the solution extracted with Et2O, the aqueous portion made alk. with concentrated NaOH, and the resulting emulsion kept 1 day gives 0.51 g. papaverine, m. 147° (CHCl3-petr. ether). Trans-cinnamoyl chloride (3 g.) in 15 cc. Et2O is added dropwise to 2 g. II in 50 cc. Et2O with vigorous stirring, the solution made alk. with dilute NaOH after a solid forms, and dl-trans-N-[β-hydroxy-β-(p-methoxyphenyl)]ethylcinnamide (VI) (1.2 g.), m. 177-8°, filtered, washed (H2O), and recrystallized from EtOAc. VI is identical with natural aegeline. The experimental process involved the reaction of N-(2-Hydroxy-2-(4-methoxyphenyl)ethyl)cinnamamide(cas: 456-12-2).Electric Literature of 456-12-2
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. Electric Literature of 456-12-2
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics