Sodium Hydroxide → 3-Azido-N-(3-(dimethylamino)propyl)-N,3-dimethylbutanamide

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Reaction Steps

To a stirred ice cold solution of N1,N1,N3-trimethylpropane-1,3-diamine (5.0 g, 1 equiv, 43.0 mmol) and DIEA (11.2 mL, 1.5 equiv, 64.5 mmol) in anhydrous DCE (200 mL) was added 3-azido-3-methylbutanoyl chloride (6.95 g, 43.0 mmol) in small portions. The reaction was stirred and left at 0° C. for 1 h. Aqueous NaOH (5N, 4 equiv, 34.5 mmol) was added to the reaction mixture. The solvent and DIEA was removed via rotovap to give an oily aqueous mixture. The contents of the flask was poured into a separatory funnel and extracted with DCM (2×100 mL). The organic layer was dried over anhydrous MgSO4, filtered, concentrated and dried under high vacuum to give a crude oil (8.71 g, 84.0%). This material was used without further purification. 1H NMR (D2O, 400 MHz): δ 1.34 (t, J=7.2, 3H), 1.43 (s, 6H), 2.11-2.15 (m, 2H), 3.09 (s, 3 H), 3.35 (s, 2H), 3.41 (dt, J=7.2, 4H). LRMS (ESI+) for C11H23N5O (241.2); Found: 241 (M+).

Provenance & Evidence