L-Alanine, N,N-dimethyl-, hydrazide synthesis

Yield:-

Reaction Conditions:

with potassium carbonate;dimethyl amine;hydrazine in tetrahydrofuran;

Steps:

A A.

A. N-Amino-2-(Dimethylamino)Propanamide Two equivalents of a 2.0 N commercial solution of dimethylamine in THF (36.0 mL, 35.91 mmol) were added to methyl 2-bromopropanoate (2.672 mL, 23.94 mmol), followed by one equivalent of potassium carbonate (5.0 g, 36.1 mmol). The heterogeneous mixture was stirred at room temperature overnight. The solution was filtered and transferred into a sealed tube. Anhydrous hydrazine was added (1.161 mL, 23.94 mmol). The reaction mixture was heated to reflux temperature overnight. The white precipitate that formed was filtered and the solution was concentrated. The title compound was used without further purification: ¹H NMR (DMSO d₆) δ 8.91 (br s, 1H), 3.56 (br s, 2H), 2.89 (q, 1H), 2.15 (s, 6H), 1.06 (d, 3H); ES-MS (m/z) 132 [M+H]⁺.

References:

US2002/103229,2002,A1