4-(4-iodophenethyl)morpholine synthesis

Yield:100839-46-1 54.3%

Reaction Conditions:

Stage #1: 2-(4-iodophenyl)-1-morpholin-4-ylethanonewith sodium tetrahydroborate;boron trifluoride diethyl etherate in tetrahydrofuran at 0 - 20;
Stage #2: with water in tetrahydrofuran at 0 - 20; for 16 h;
Stage #3: with water at 0;

Steps:

4- [2-(4-Iodo-phenyl)-ethyl] -morpholine

4- [2-(4-Iodo-phenyl)-ethyl] -morpholine: BF₃.Et₂0 (6.43 g, 45.3 mmol) was added to a solution of 2-(4-iodo-phenyl)-l-morpholin-4-yl- ethanone (3.0 g, 9.06 mmol) in THF (75 mL) at 0 °C, stirred for 30 min, then NaBFL, (1.72 g, 45.3 mmol) was added at 0 °C. The reaction mixture was slowly warmed to RT. After 16 h the reaction mixture was cooled to 0 °C, quenched with ice-cold water, extracted with EtOAc (2 x 100 mL). The organic layer was washed with brine solution (50 mL), dried over anhydrous Na₂S0₄ and solvent was evaporated under reduced pressure. The crude compound was purified by column chromatography using 100-200 mesh silica gel, eluted with 20-30% EtOAc in pet- ether to afford 1.56 g (Yield: 54.3%) of the title compound as a yellow solid. 1H NMR (DMSO-dg, 400 MHz, TMS) δ: 7.64-7.62 (2H, d), 7.07-7.05 (2H, d), 4.11-4.07 (2H, q), 3.58 (4H, br, s), 2.67 (2H, br, s), 2.46 (4H, br, s).

References:

WO2014/106612,2014,A1 Location in patent:Page/Page column 31-32