Sodium Hydroxide → 3,4-Dimethoxybenzenepropanamine

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(3,4-dimethoxy-phenyl)-propionamide (11.1 g, 53.0 mmol) in anhydrous THF (400 ml) is slowly added to a stirred, ice-cooled suspension of LiAlH4 (4.02 g, 106 mmol) in anhydrous THF (170 mL). Upon completion of the addition, the mixture is stirred at reflux for 2 h. After cooling to 0° C., H2O (5 mL) and NaOH 1N (5 mL) are added dropwise to decompose the excess of hydride. The suspension is filtered and evaporated. The residue is partitioned between H2O (40 mL) and CH2Cl2 (100 mL). The organic layer is washed with saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure to give the title compound as a yellow oil.

Provenance & Evidence