N-Methylbutylamine → HCID 60134574, compound

Participants

Reaction Steps

To a stirred ice cold solution of N-methylbutan-1-amine (8.88 mL, 2 equiv, 74.4 mmol) in anhydrous DCE (65 mL) was added 3-azido-3-methylbutanoyl chloride (6.02 g, 37.2 mmol) in small portions over 5 min. The reaction was removed from the ice bath and stirred at room temperature for 1 h. The reaction mixture was poured into a separatory funnel and washed with 1 M HCl (2×100 mL). The organic layer was separate and dried over anhydrous MgSO4, filtered, concentrated and dried under high vacuum to give a yellow oil (7.11 g, 90.1%). This material was used without further purification. 1HNMR (CDCl3, 400 MHz): δ 0.91-0.98 (m, 3H), 1.27-1.37 (m, 2H), 1.46 (s, 6H), 1.47-1.57 (m, 2H), 2.49 (s, 2H), 2.92 (s, 1.35H), 3.02 (s, 1.48H) methyl rotamers, 3.28-3.39 (m, 2H). LRMS (ESI+) for C10H20N4O (212.2); Found: 213 (MH+).

Provenance & Evidence