3-(4-Methylpiperazin-1-yl)phenyl]methanol

Synthesis

109-01-3

15852-73-0

123987-13-3

GENERAL STEPS: To a solution of 3-bromobenzyl alcohol (570 mg, 3.05 mmol) in tetrahydrofuran (THF, 5 mL) was added lithium hexamethyldisilanilide (LHMDS, 7.43 mL, 7.43 mmol) and the reaction mixture was stirred for 30 min at room temperature. Ru-phos precatalyst (97 mg, 0.133 mmol), dicyclohexyl (2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (61.9 mg, 0.133 mmol) and N-methylpiperazine (0.441 mL, 3.98 mmol) were subsequently added. The reaction system was degassed with a stream of nitrogen and then heated to 75 °C for 1 hour. After completion of the reaction, the reaction mixture was diluted with dichloromethane (DCM) and washed with water. The organic layer was concentrated under reduced pressure and purified by silica gel column chromatography (eluent: 0-20% methanol/DCM) to afford the target product (3-(4-methylpiperazin-1-yl)benzyl alcohol (506 mg, 80% yield). Mass spectrum (electrospray positive ionization mode, ES+): theoretical molecular weight of C12H18N2O 206, measured value 207 [M+H]+.

References