Example 2
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In a nitrogen-filled glovebox, Armeen M2HT, a di-hydrogenated tallow alkyl methyl amine available from Akzo-Nobel. (5.36 g, 10.0 mmol, 1 equiv.) was dissolved in hexane (150 mL). A 2 M solution of HCl in diethyl ether (5.0 mL, 10.0 mmol, 1 equiv.) was slowly added dropwise to the stirring amine solution, resulting in the immediate precipitation of a white solid. The suspension was stirred at room temperature for 15 min. The precipitated solid was voluminous and fine, producing a thick gel-like suspension. The suspension was attempted to be filtered, however it did not pass through the filter. The suspension was transferred back into a glass jar and dried in vacuo to yield 4.76 g of a white solid, a 83% yield.
1H NMR (400 MHz, Toluene-d8) δ 13.02-12.71 (m, 1H), 2.90 (dtd, J=43.2, 12.4, 6.8 Hz, 4H), 2.67 (d, J=4.7 Hz, 3H), 1.72 (ddt, J=50.3, 13.3, 6.7 Hz, 4H), 1.32 (d, J=22.5 Hz, 60H), 0.91 (t, J=6.6 Hz, 6H). 13C NMR (101 MHz, Toluene-d8) δ 54.75, 39.08, 32.03, 30.00, 29.98, 29.95, 29.92, 29.86, 29.53, 29.48, 27.04, 23.62, 22.77, 13.96.