A solution of 21.0 g (0.15 mol) of 2-chlorobenzaldehyde in 100 ml of ethanol
(95%) was added to a solution of 20.5 g (0.152 mol) of D-1-phenyl-2-aminopropane in 100 ml of ethanol (95%). After standing for 15 h at room
temperature, the ethanol was driven off, and the oily residue was then
distilled to yield 36.2 g (94%) of D-N-(2-chlorobenzylidene)-2-amino-1-
phenylpropane, boiling point 142°-146°C/0.1 mm Hg.
To the solution of 36.0 g (0.14 mol) of D-N-(2-chlorobenzylidene)-2-amino-1-
phenylpropane in 200 ml of dry methanol were added, in portions, 5.3 g (0.14
mol) of sodium borohydride. The mixture was stirred for 1 h at room
temperature, and refluxed for 1 h water (100 ml) was then added and the
methanol was removed in vacuo. After acidifying carefully with dilute
hydrochloric acid, the solution was made alkaline by dilute sodium hydroxide,
and extracted with ether. 33.0 g (90%) of D-N-(1-phenyl-2-propyl)-2-
chlorobenzylamine, boiling point 132°-134°C/0.1 mm Hg, were obtained by
distillation.
