(1-Amino-2-methylpropan-2-yl)(methyl)amine synthesis

Yield:116577-09-4 72%

Reaction Conditions:

Stage #1: 2-methylamino-2-methylpropanenitrilewith lithium aluminium tetrahydride in diethyl ether at 0; for 3 h;Heating / reflux;
Stage #2: with sodium hydroxide;water in diethyl ether at 0;

Steps:

A.18 2,N2-Dimethyl-propane-1,2-diamine.

[0203] Crude 2-methyl-2-methylamino-propionitrile (2.00 g, 20.4 mmol; Gabriel, Chem. Ber., 47, 2922-2925 (1914) and 1H NMR matched Stork et al., J. Am. Chem. Soc.; 96; 1974; 5787-5791 (1974)) was added to a suspension of LiAlH4 (1.55 g, 20.38 mmol) in ether (40 mL) at 0° C. The resultant mixture was heated at reflux for 3 hours, then cooled to 0° C., and quenched with H2O (4 mL) and 2N NaOH (3 mL). After a few minutes of stirring, the granular white solids were filtered off. The filtrate was dried over Na2SO4, filtered, and concentrated in vacuo to afford 1.5 g of a colorless oil in 72% yield, which was used without further purification. [0204] 1H NMR (CDCl3): δ 2.47 (2H, s), 2.22 (3H, s), 0.94 (6H, s).

References:

US2003/225147,2003,A1 Location in patent:Page 19-20