Putrescine → HCID 89824741, compound

Participants

Reaction Steps

Putrescine (9.45 g, 107 mmol) was dissolved in acetonitrile (200 mL) with K2CO3 (14.79 g, 107 mmol) and stirred under N2. Mesylate 22 (6.03 g, 21.4 mmol) dissolved in acetonitrile (60 mL) was added dropwise over 30 min while stirring under N2. After 30 min, the reaction mixture was brought to reflux and stirred overnight. The reaction mixture was then cooled, solid K2CO3 was filtered off and the filtrate concentrated in vacuo. The residue was re-dissolved in CH2Cl2 (200 mL) and washed six times with sat. aqueous Na2CO3 to remove the unreacted putrescine. The organic layer was then dried over anhydrous Na2SO4, filtered, and concentrated to give the product 23 as a clear oil that was used in the next step without further purification, yield: 5.31 g (90%); 1H NMR (CDCl3) δ 3.21 (t, 2H), 2.84 (s, 3H), 2.71 (t, 2H), 2.62 (t, 4H), 1.40-1.60 (m, 17H).

Provenance & Evidence