Benzylamine → HCID 17810233, compound

Participants

Reaction Steps

To a solution of 10-phenyldecanoic acid (1.101 g, 4.43 mmol) in 20 mL of CH2Cl2 at room temperature was added oxalyl chloride (1.41 g, 11.08 mmol) and 1 drop of DMF, and the reaction mixture was stirred for 1 hour under nitrogen. The CH2Cl2 and excess oxalyl chloride were evaporated. The reaction was redissolved in CH2Cl2 and benzylamine (1.42 g, 13.3 mmol) and 2 mL of saturated aqueous NaHCO3 were added and the reaction stirred for 12 hours. The reaction was taken up in EtOAc and washed with 1N HCl×2, followed by saturated aqueous NaCl, and evaporated to give 1.462 g (98%) of an oil that was used without further purification. 1H NMR (CDCl3, 300 MHz) δ 1.30 (m, 10H), 1.55-1.72 (m, 4H), 2.20 (t, 2H), 2.59 (t, 2H), 4.45 (d, 2H), 5.68 (bs, 1H), 7.12-7.38 (m, 10H). MS (DCl--NH3) m/e (M+H)+ 338.

Provenance & Evidence