Methanol → Methyl 4-(2-aminoethyl)benzoate

Temperature

22 °C

To a solution of 2.02 g (10.0 mmol) of 4-(2-aminoethyl)benzoic acid hydrochloride in 25 mL of methanol was added 1.5 mL of H2SO4. The mixture was heated to reflux and became a homogeneous solution after 1 h. The solution was refluxed for about 16 h, cooled to 22° C. and concentrated to about 10 mL by evaporation. The solution was diluted with 100 mL of water, made basic with 1 N NaOH and extracted with 100 mL of dichloromethane (DCM). The aqueous layer was back-extracted with DCM (4×100 mL). The combined extracts were dried (Na2SO4) and evaporated to give methyl 4-(2-aminoethyl)benzoate as a colorless oil. The material was used directly in the subsequent transformation.

1. temperatureThe mixture was heated
2. temperatureto reflux
3. customafter 1 h
4. temperatureThe solution was refluxed for about 16 h
5. concentrationconcentrated to about 10 mL by evaporation
6. additionThe solution was diluted with 100 mL of water
7. extractionextracted with 100 mL of dichloromethane (DCM)
8. extractionThe aqueous layer was back-extracted with DCM (4×100 mL)
9. dry with materialThe combined extracts were dried (Na2SO4)
10. customevaporated

ORD record

ord-ab2dff61208649459be34f0a6407ca45

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227918B2