N,N-Dimethylpropargylamine → HCID 68213355, compound

Participants

Reaction Steps

A solution of dilinoleyl methyl azide (500 mg, 0.90 mmol) and 3-dimethylamino-1-propyne (75 mg, 0.90 mmol) in H2O and tert-butyl alcohol (1:1, 12 mL) was treated with sodium ascorbate (0.090 mmol, 17.94 taken from a 1M solution in water), followed by CuSO4.5H2O (2.3 mg, dissolved in 30 μL of water) and stirred (96 h). The solution was then diluted with H2O (50 mL) and extracted with CH2Cl2 (3×), dried (Na2SO4), filtered, concentrated and purified via column chromatography (2%→4% MeOH/CH2Cl2) to yield the title compound as a colorless oil (524 mg, 91%). 1H NMR (400 MHz, CDCl3, δH) 7.76 (br. s, 1H), 5.47-5.25 (m, 8H), 4.48 (p, 1H), 3.80 (br. s, 2H), 2.75 (app. t, 4H), 2.49 (s, 6H), 2.15-2.00 (m, 8H), 1.91-1.75 (m, 4H), 1.40-1.12 (m, 34H), 1.11-0.98 (m, 2H), 0.85 (t, 6H). FW 637.08, C42H76N4.

Provenance & Evidence