Benzaldehyde → HCID 12601130, compound

20 g. of 2-methylamino-ethylamine in 100 ml. of absolute benzene was stirred with 28.7 g. of benzaldehyde. The mixture warmed up somewhat and became yellow. The benzene was evaporated in vacuo and the residue distilled under reduced pressure in a Hickmann-flask. After a little forerun, the desired fraction distilled at 106°-107°/13 mm. The N-benzylidene-N'-methylethylenediamine was obtained as a colorless oil of nD22 = 1.5452 and a U.V.-absorption maximum at 245 mμ. 25 g. of this product were dissolved in 150 ml. methylene chloride and thereto were added 16.5 g. of triethylamine and while stirring and cooling in an ice bath, 26.7 g. of carbobenzoxy chloride in 100 ml. of methylene chloride in such a way that the temperature did not rise over 20°. The mixture was stirred for 3 hours at room temperature and shaken with 100 ml. of water. The methylene chloride layer was washed three times with water and concentrated in vacuo. The yellow oil obtained was well mixed with 100 ml. of ether and 100 ml. of 6 N sulfuric acid for one hour at room temperature. The layers were separated, the aqueous layer extracted five times more with 30 ml. ether each time. To this ether extracts were added, while cooling on an ice bath, 50 g. of solid potassium hydroxide. The oily product was extracted with methylene chloride, the extract concentrated and the residue distilled under reduced pressure. The desired product distilled, after a short forerun, at 105°-112° /0.04 mm. as a colorless oil of nD24 = 1.5355.

1. temperatureThe mixture warmed up somewhat
2. customThe benzene was evaporated in vacuo
3. distillationthe residue distilled under reduced pressure in a Hickmann-flask
4. distillationAfter a little forerun, the desired fraction distilled at 106°-107°/13 mm

ORD record

ord-6e2d6ae254e4450aa76995e2e53fbc61

Source dataset

uspto-grants-1976_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03931268