Hydrochloric Acid → (4-Tert-butyl-benzyl)-[2-(3-ethoxy-phenyl)-ethyl]-amine

0.38 ml of 4-tert-butylbenzaldehyde (2.25 mmol) and 0.245 ml of 3-ethoxyphenethyl-amine (1.5 mmol) were dissolved in 5 ml methanol at rt, and after stirring for 30 min at rt, were refluxed for 2 h. After cooling down to rt, 85 mg (2.25 mmol) of sodium borohydride were added and after 10 min stirring at rt, the reaction mixture was then refluxed for 3 h. After cooling down to rt, the reaction mixture was treated with 0.15 ml 1 N HCl and concentrated in vacuo. The residue was diluted with water/EtOAc. After separation of the organic phase, the aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered off and concentrated in vacuo. The residue, 461 mg of a light yellow oil, was not further purified and used directly in the next step.

1. temperaturewere refluxed for 2 h
2. temperatureAfter cooling down to rt
3. stirringstirring at rt
4. temperaturethe reaction mixture was then refluxed for 3 h
5. temperatureAfter cooling down to rt
6. concentrationconcentrated in vacuo
7. additionThe residue was diluted with water/EtOAc
8. customAfter separation of the organic phase
9. extractionthe aqueous phase was extracted with EtOAc
10. washthe combined organic phases were washed with brine
11. dry with materialdried with magnesium sulfate
12. filtrationfiltered off
13. concentrationconcentrated in vacuo
14. customThe residue, 461 mg of a light yellow oil, was not further purified

ORD-Eintrag

ord-c258f04f4ef14c419e3ece5bac9481e3

Quelldatensatz

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07259183B2