1-Chloro-4-(chloromethyl)benzene → HCID 53361024, compound

Participants

Reaction Steps

To a DMF (5 mL) solution of (E)-3-(3,5-dimethyl-4-{[5-(pyridin-4-ylmethoxy)-pyridin-2-yl]oxy}phenyl)-1-{4-[4-(2-hydroxyethyl)benzyl]piperazin-1-yl}prop-2-en-1-one (400 mg) was added NaH (35.9 mg, 60% in mineral oil) at 0° C., then the resultant mixture was stirred for 1 hour. To the mixture was added 4-chlorobenzyl chloride (0.093 mL) at 0° C., then the resultant mixture was stirred at room temperature for 3 hours. The mixture was poured into saturated aqueous NH4Cl, and extracted with AcOEt. The organic layer was washed with H2O and saturated aqueous NaCl, dried over anhydrous Na2SO4, and evaporated. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1 to 1/0 and then AcOEt/MeOH=4/1) to afford (E)-1-[4-(4-{2-[(4-chlorobenzyl)oxy]ethyl}benzyl)piperazin-1-yl]-3-(3,5-dimethyl-4-{[5-(pyridin-4-ylmethoxy)pyridin-2-yl]oxy}phenyl)prop-2-en-1-one as a pale yellow amorphous powder (91 mg).

Provenance & Evidence