L-CARNITINE:HCL, O-OCTANOYL synthesis

Yield:54377-02-5 81.1%

Reaction Conditions:

in chloroacetic acid at 50 - 70;

Steps:

3 Example 3

20.0 g L-Carnitine.HCl and 25.3 g mono-chloracetic acid are filled in the equipment and heated up to 70 °C. After complete melting the solution is cooled down to 50 °C. 22.0 g octanoyl chloride is slowly dosed over 30 minutes and the solution is heated up to 70 °C and stirred for 3 hours. After dosing 30.8 g isopropanol at room temperature slowly, exothermic, 104.5 g ethyl acetate is added and the suspension is cooled down to 3 °C overnight. The solid is filtered out and washed with 147.8 g isopropanol/ethyl acetate (1:2.7) and dried at 50 °C and 24 mbar overnight. 25.4 g Octanoyl-L-carnitine.HCl is obtained. The yield comes to 81.1%. mp 178-181 °C H-NMR (500 MHz, DMSO) δ 0.85 (t, 3 H), 1.25 (m, 8 H), 1.5 (m, 2 H), 2.3 (m, 2 H), 2.7 (d, 2 H), 3.1 (s, 9 H), 3.65 (d, 1 H), 3.8 (dd, 1 H), 5.45 (m, 1 H)

References:

EP2216321,2010,A1 Location in patent:Page/Page column 2-3