Water → 3-[4-(Benzyloxy)-3-methoxyphenyl]propan-1-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(4-benzyloxy-3-methoxy-phenyl)-propionamide (7.85 g, 27.53 mmol) in anhydrous THF (210 ml) was slowly added to a stirred, ice-cooled suspension of LiAlH4 (2.09 g, 55.07 mmol) in anhydrous THF (90 ml). Upon completion of the addition, the mixture was stirred at reflux for 1 h. After cooling to 0° C., H2O (15 ml) was added dropwise to decompose the excess of hydride, and the resulting suspension was then filtered. The residue after evaporation was partitioned between H2O (50 ml) and CH2Cl2 (100 ml). The organic layer was washed with NaHCO3 and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure to give the crude. amine (6.03 g, 22.22 mmol, 81%) as a yellow oil.

Provenance & Evidence