One hundred and six grams (1 mole) of benzaldehyde (Note
1) and
107 g. (1 mole) of m-toluidine are mixed in a suitable flask; the temperature rises to about 60° (Note
2) and (Note
3). The mixture is cooled below 35° in cold water,
200 ml. of ether is added, and the solution is placed in the
steel reaction vessel of a high-pressure hydrogenation apparatus.
Eight to ten grams of Raney nickel catalyst
(p. 181) is added, the bomb is closed, and
hydrogen is admitted up to 1000 lb. pressure (Note
4). The bomb is shaken continuously at room temperature for 15 minutes (Note
5). The contents are removed, and the bomb is washed out with two
200-ml. portions of ether. After the catalyst has been separated by filtration (Note
6), the
ether is removed by distillation and the product is distilled from a
modified Claisen flask (Note
7). After a small fore-run the
N-benzyl-m-toluidine boils at
153–157° /4 mm.;
315–317° /760 mm. The yield is
175–185 g. (
89–94%) (Note
8) and (Note
9).