Organic Syntheses, CV 4, 564
Submitted by C. V. Wilson and J. F. Stenberg
1.
Checked by N. J. Leonard and C. W. Schimelpfenig.
1. Procedure
In a
5-l. three-necked flask, fitted with a
ball-joint sealed stirrer and a
Soxhlet extractor (70 mm. internal diameter × 300 mm. length of body) carrying a large-capacity
condenser, are placed
1.8 l. of dry ether (Note
1) and
38 g. (1 mole) of finely divided lithium aluminum hydride (Note
2). In the Soxhlet cup is placed
160 g. (0.75 mole) (Note 3) of N-methyllauramide (m.p.
67–69°) (Note
4). The mixture is heated under gentle reflux with efficient stirring over a 5-hour period and then stirred overnight at room temperature (Note
5); the
N-methyllauramide is extracted from the cup during the first 3 hours.
The excess
lithium aluminum hydride and the metallic complexes are decomposed by the careful addition of 82 ml. of distilled water, from a
dropping funnel, to the well-stirred mixture. The reaction mixture is stirred for an additional 30 minutes, filtered with suction, and the solid is washed with several
100-ml. portions of ether. After the
ether is removed from the filtrates, the residual oil is distilled under reduced pressure. The yield of
laurylmethylamine, a colorless liquid boiling at
110–115°/1.2–1.5 mm., is
121–142 g. (
81–95%) (Note
6).
2. Notes
3. If a Soxhlet extractor having a smaller capacity is employed, the cup will have to be recharged during the course of the reaction.
5. Stirring overnight is a matter of convenience. In the preparation of
methylnonylamine, refluxing for an hour after the addition of the amide was found by the submitters to be sufficient.
3. Discussion
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