Piperazine → 1-[6-(Piperazin-1-yl)naphthalen-2-yl]ethan-1-one

Anhydrous piperazine (7 g, 81.3 mmol; dried in a vacuum desiccator over KOH-drierite mixture for 3 days) was dissolved in a mixture of dry, freshly distilled toluene and hexamethyl phosphoric amide (HMPA), 25 mL each. To the solution was added 556 mg (80.1 mmol) of lithium rod, cut in small pieces under argon atmosphere, and the mixture was stirred under argon for 24 hours, during which time all lithium has dissolved. Vacuum-dried 1-(6-methoxy-2-naphthyl)-1-ethanone (prepared as described in Arsenijevic et al., Org. Synth. Coll. 1988 6:34-36, the disclosure of which is incorporated herein by reference) (3.5 g, 17.5 mmol) was added, and stirring was continued for additional 65 hours. After quenching with 300 mL of water, extraction with dichloromethane (3×300 mL), drying with anhydrous magnesium sulfate, and evaporation, a mixture of white and yellow solids was obtained. Extraction with 300 mL of hot methanol gave raw product, 1-(6-piperazino-2-naphthyl)-1-ethanone, which was purified by column chromatography (70-230 mesh silica, 25×120 mm, 5% methanol in dichloromethane). The yield was 1.54 g (35%). After recrystallization from ethyl acetate, the sample melted at 170.5-172° C.

1. dry with materialdried in a vacuum desiccator over KOH-drierite mixture for 3 days)
2. dissolutionwas dissolved in a mixture
3. customof dry
4. dissolutionhas dissolved
5. additionwas added
6. customAfter quenching with 300 mL of water, extraction with dichloromethane (3×300 mL)
7. dry with materialdrying with anhydrous magnesium sulfate, and evaporation
8. additiona mixture of white and yellow solids
9. customwas obtained
10. extractionExtraction with 300 mL of hot methanol

ORDレコード

ord-deaa9b0a4aae4aa296572d54c6a593c7

出典データセット

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06660530B2