Acetyl chloride → HCID 23441041, compound

Participants

Reaction Steps

Compound No. 296 (16 mg, 18%) was prepared from 1-[3-hydroxy-3-(3-hydroxyphenyl)-3-phenylpropyl]homopiperazine (Compound No. 295, 78 mg, 0.24 mmol) and acetyl chloride (19 mg, 1.0 equiv). Acetyl chloride and Et3N (121 mg, 1.2 mmol, 5.0 equiv) were added to a solution of 1-[3-hydroxy-3-(3-hydroxyphenyl)-3-phenylpropyl]homopiperazine (Compound No. 295) in CH3CN (2.0 mL). The reaction mixture was stirred at room temperature for 30 min. saturated aqueous NaHCO3 (10 mL) was added to the reaction mixture and the mixture was extracted with AcOEt (3×15 mL). The combined extracts were dried over MgSO4. The solvent was removed under reduced pressure to afford an oil which was purified by column chromatography (SiO2, 3-10% CH3OH/CH2Cl2) to give 1-acetyl-4-[3-hydroxy-3-(3-hydroxyphenyl)-3-phenylpropyl]homopiperazine (Compound No. 296): 16 mg, 18% yield, colorless oil: RPLC tR=4.75 min (89%), 220 nm (Method B); ESI/MS m/e 369.3 (M++H, C22H29N2O3).

Provenance & Evidence