Palmitoyl chloride → Palmitamidopropyl diethylamine

Participants

Reaction Steps

To a solution of 3-diethylaminopropylamine (4.13 g, 31.7 mmole) in methylene chloride (50 mL) was added palmitoyl chloride (9.15 g, 33.3 mmole) in small portions. The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was dissolved in 1N aqueous sodium hydroxide (90 mL), chloroform (100 mL) and methanol (200 mL). The solution was transferred to a separatory funnel then chloroform (100 mL) and IN aqueous sodium hydroxide (100 mL) was added and the layers separated. The aqueous layer was extracted twice with chloroform (100 mL portions). The solution was transferred to a separatory funnel then chloroform. The organic layer was dried over magnesium sulfate and the salts removed by filtration. The solvent was removed under reduced pressure to give the title compound (11.6 g, 100%) as a gum. 1H NMR (300 MHz, CDCl3): δ0.881 (3H, t, J=6.6 Hz), 1.053 (6H, t, J= 7.1 Hz), 1.252 (24H, bs), 1.56 to 1.67 (2H, m), 2.129 (2H, t, J=7.7 Hz), 2.50 to 2.57 (6H, m), 3.31 to 3.37 (2H, m), and 7.392 (1H, bs). IR (neat): 3307, 3219, 3152, 3085, 2949, 2920, 2850, 1734, 1642, 1082 cm-1. Analysis calculated for C23H48N2O.3/4H2O: C, 74.94; H, 13.12; N, 7.59. Found: C, 74.68; H, 13.11; N, 7.52.

Provenance & Evidence