Diethylaminoalkylamino derivatives of carbocyclic series was written by Wojahn, Hans;Erdelmeier, Karl. And the article was included in Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft in 1942.Synthetic Route of C10H15NO The following contents are mentioned in the article:
Et2NCH2Ac (7 g.) and 5.5 g. m-H2NC6H4OH (I) in 10 cc. EtOH, heated on the water bath for 10 min. and the solution catalytically reduced, give 3 g. of m-hydroxy-[N-(2-diethylamino-1-methylethyl)amino]benzene (II), b16 185-90°; di-HCl salt, m. 193-4°. I (5.5 g.) and 7.5 g. Et2N(CH2)3Cl, refluxed in 50 cc. C6H6 for 12 h., give 6 g. of the N-(3-diethylaminopropyl) isomer of II, b16 185°; dipicrolonate, m. 214-15°. Et2NCH2CMe2CHO gives the N-(3-diethylamino-2,2-dimethylpropyl) homolog, b14 180-5°; dipicrolonate, m. 234° (decomposition). 5-Diethylamino-2-pentanone (5.5 g.) and 3.5 g. of I yield 2 g. of the N-[4-diethylamino-1-methylbutyl] homolog of II, b16 175-8°; dipicrolonate, m. 226°. o-HOC6H4CHO and Et2NCH2CH2NH2, heated 10 min. on the water bath and the Schiff base catalytically reduced, give a poor yield of o-hydroxy-N-(2-diethylaminoethyl)benzylamine (III), b15 181°; dipicrate, m. 196-7° (decomposition); dipicrolonate, m. 211-12°; the m-HO isomer of III, b14 184-6°; dipicrolonate, m. 197-9°; the p-HO isomer, b13 180-2°; dipicrolonate, m. 209°; N-(3-diethylaminopropyl) homolog (IV) of III, b14 184-7° (3-g. yield from 3.5 g. of o-HOC6H4CHO); the m-HO isomer of IV, b16 200-3°; dipicrolonate, m. 213-15°. o-MeOC6H4CH2NH2 (5.5 g.) and 5.4 g. of Et2NCH2CH2Cl in 20 cc. EtOH containing 5.5 g. AcONa, refluxed 8 h., give 5 g. of o-methoxy-N-(2-diethylaminoethyl)benzylamine (V), b14 204-6°; dipicrolonate, yellow, m. 205-7°; p-MeO isomer, b18 203-5°; dipicrate, m. 140-1°. o-EtO homolog of V, b14 205-7°; dipicrate, m. 154°. o-MeOC6H4CHO and Et2N(CH2)3NH2 give o-methoxy-N-(3-diethylaminopropyl)benzylamine (VI), b16 177°; dipicrolonate, m. 212-14°; m-MeO isomer, b13 191°; dipicrolonate, m. 210-11°; p-MeO isomer, b16 170°; dipicrolonate, m. 206°; o-EtO homolog of VI, b14 177°; dipicrolonate, m. 212-14°. o-Methoxy-N-(3-diethylamino-2,2-dimethylpropyl)benzylamine (VII), b14 186°; dipicrolonate, m. 208-10°; m-MeO isomer, b13 186°; dipicrolonate, m. 204°; p-MeO isomer, b14 205°; dipicrolonate, m. 217°. o-EtO homolog of VII, b14 203-4°; dipicrolonate, m. 202°. o-Methoxy-N-(4-diethylamino-1-methylbutyl)benzylamine, b14 190-4°; dipicrolonate, m. 149°; m-MeO isomer, b15 207-13°; dipicrolonate, m. 149°; p-MeO isomer, b14 203-8°; dipicrolonate, m. 204°. o-MeOC6H4CHO, 15 g. MeNH2.HCl, 15 g. HCO2Na and 20 g. anhydrous HCO2H, heated at 150° for 3-4 h., give 13 g. of the formyl derivative, b14 180-5°; refluxing with 20% HCl for 4 h. gives 8 g. of N-methyl-o-methoxybenzylamine (VIII), b. 226°; picrolonate, m. 176°; p-MeO isomer, b. 238°; formyl derivative, b. 317°. N-Ethyl-o-methoxybenzylamine (IX), b. 238°; formyl derivative, b14 185-90°; picrolonate, m. 186-80°; m-MeO isomer, b. 245°; formyl derivative, b14 185-90°; picrolonate, m. 190°; p-MeO isomer, b. 244°; formyl derivative, b14 187-90°; picrolonate, m. 210°. VIII (3.1 g.), heated with 2.8 g. Et2NCH2CH2Cl and 2.8 g. AcONa in 20 cc. AcOH for 8 h. on the water bath, gives 50% of N-methyl-N-(2-diethylaminoethyl)-o-methoxybenzylamine (X), b14 170-5°; dipicrolonate, m. 166°; p-MeO isomer, b14 172-7°; dipicrolonate, m. 195°. N-Et homolog of X, prepared from IX, b14 185-90°; dipicrolonate, m. 187°; m-MeO isomer, b16 180-5°; dipicrolonate, m. 200°; p-MeO isomer, b14 175-80°; dipicrolonate, m. 195°. VIII and Et2N(CH2)3Cl give N-methyl-N-(3-diethylaminopropyl)-o-methoxybenzylamine (XI), b16 175-80°; dipicrolonate, m. 177°; p-MeO isomer, b14 195-200°; dipicrolonate, m. 190°. IX gives the N-Et homolog of XI, b14 187-9°; dipicrolonate, m. 170°; p-MeO isomer, b14 185-90°; dipicrolonate, m. 210°. This study involved multiple reactions and reactants, such as N-(3-Methoxybenzyl)ethanamine (cas: 140715-61-3Synthetic Route of C10H15NO).
N-(3-Methoxybenzyl)ethanamine (cas: 140715-61-3) belongs to ethers. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Synthetic Route of C10H15NO
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem