Benzaldehyde → N-benzyl-4-fluoroaniline

Participants

Reaction Steps

A solution of 4-fluoroaniline (4.7 ml, 50 mmol), benzaldehyde (5.3 g, 50 mmol) and one crystal p-toluene-sulfonic acid is refluxed using a Dean-Stark® apparatus until no more water is collected and the mixture is concentrated in vacuo. The crude product is dissolved in 100 ml 96% ethanol and added sodium borohydride (4.0 g, 100 mmol) and stirred for 1 hour. Most of the ethanol is removed in vacuo and the residue is taken up in water and 15 g of potassium hydroxide in 50 ml water is added, causing the amine to crystallize. The product is recrystallized from methanol/water (in a ratio of 4 to 1) yielding the title compound as white crystals. Mp 38°-39° C.

Provenance & Evidence