Dodecylamine → N-Dodecyl-3,5-bis(3-chlorophenyl)-4-(2-hydroxyethoxy)benzamide

Temperature

0 °C

To a flamed dried round bottom flask with dodecyl amine (0.519 g, 2.80 mmol) and THF (8 mL) cooled to 0° C. was added n-BuLi (1.12 mL, 2.5 M in hexane, 2.80 mmol) dropwise over a 5 min. period. The resulting solution was stirred at this temperature for 40 min. and then cooled to −45° C. To this solution was added dropwise a solution (at 0° C.) of 3,5-bis-(m-chlorophenyl)4-(2-hydroxyethoxy)benzoic acid ethyl ester (0.302 g, 0.700 mmol) in THF (8 mL) over 5 min. This final mixture was stirred and warmed to room temperature over 30 min. At this point, the reaction mixture was quenched with H2O (3 mL) and diluted with EtOAc (40 mL). The organic layer was washed with 1 N HCl (3×7 mL), brine (7 mL), and H2O:brine (1:1, 14 mL) and then dried (Na2SO4). After concentration, the residue was purified by flash chromatography (0 to 15% EtOAc/hexane gradient) to afford the product (0.286 g, 72%) as an oily white solid; 1H NMR (DMSO-d6) δ0.86 (t, J=7.7 Hz, 3H), 1.20-1.37 (m, 18H), 1.46-1.57 (m, 2H), 3.13 (dd, J=6.9, 11.5 Hz, 2H), 3.20-3.33 (m, 4H), 4.46 (t, J=6.2 Hz, 1H), 7.43-7.57 (m, 4H), 7.59-7.63 (m, 2H), 7.68-7.73 (m, 2H), 7.89 (s, 2H), 8.67 (t, J=6.2 Hz, 1H); mass spectrum [(+) APCI], m/z 570 (M+H)+.

1. temperaturecooled to −45° C
2. temperaturewarmed to room temperature over 30 min
3. customAt this point, the reaction mixture was quenched with H2O (3 mL)
4. additiondiluted with EtOAc (40 mL)
5. washThe organic layer was washed with 1 N HCl (3×7 mL), brine (7 mL), and H2O:brine (1:1, 14 mL)
6. dry with materialdried (Na2SO4)
7. concentrationAfter concentration
8. customthe residue was purified by flash chromatography (0 to 15% EtOAc/hexane gradient)

ORD record

ord-3f7925ed931346c88dc1b1be81d8a27f

Source dataset

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06214877B1