N-Methylhexylamine → 3-azido-N-hexyl-N,3-dimethylbutanamide

To a stirred ice cold solution of N-methylhexan-1-amine (4.69 mL, 1.0 equiv, 30.9 mmol) and DIEA (7.0 mL, 1.3 equiv, 40.2 mmol) in anhydrous DCE (150 mL) was added 3-azido-3-methylbutanoyl chloride (5.0 g, 30.9 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 (3×100 mL) and saturated sodium hydrogen carbonate (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 (5.14 g, 72.0%). This material was used without further purification. 1H NMR (CDCl3, 400 MHz): δ 0.88-0.94 (m, 3H), 1.2-1.35 (m, 6H), 1.47 (d, 6H), 1.47-1.66 (m, 2H), 2.51 (s, 2H), 2.94-3.04 (d, J=40 Hz, 3 H), 3.30-3.40 (m, 2H). LRMS (ESI+) for C12H24N4O (240.2); Found: 241 (MH+).

1. customThe reaction was removed from the ice bath
2. additionThe reaction mixture was poured into a separatory funnel
3. washwashed with 1 M HCl (3×100 mL) and saturated sodium hydrogen carbonate (2×100 mL)
4. customThe organic layer was separate
5. dry with materialdried over anhydrous MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customdried under high vacuum

ORD record

ord-8c66af6d807d4acd90bb812471f73f83

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278482B2