Sodium Hydroxide → 3,4-Dimethoxybenzenepropanamine

Temperature

0 °C

A solution of 3-(3,4-dimethoxy-phenyl)--propionamide (11.09 g, 53.00 mmol) in anhydrous THF (400 ml) was slowly added to a stirred, ice-cooled suspension of LiAlH4 (4.02 g, 106.00 mmol) in anhydrous THF (170 ml). Upon completion of the addition, the mixture was stirred at reflux for 2 h. After cooling to 0° C., H2O (5 ml) and NaOH 1N (5 ml) were added dropwise to decompose the excess of hydride. The suspension was then filtered and the residue after evaporation was partitioned between H2O (40 ml) and CH2Cl2 (100 ml). The organic layer was washed with saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure to give the crude amine (7.00 g, 35.84 mmol, 68%) as a yellow oil.

1. temperaturecooled
2. additionUpon completion of the addition
3. temperatureat reflux for 2 h
4. filtrationThe suspension was then filtered
5. customthe residue after evaporation
6. customwas partitioned between H2O (40 ml) and CH2Cl2 (100 ml)
7. washThe organic layer was washed with saturated aqueous NaHCO3 and brine
8. dry with materialdried over anhydrous MgSO4
9. concentrationconcentrated under reduced pressure

ORD record

ord-872cbc1500214608914232b174f0ee3a

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07192950B2