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

HRID 650449

Reaktionsgleichung

Reaktionsgleichung von HRID 650449
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Li].CO[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:20](=[O:22])[CH3:21])[CH:14]=[CH:13]2>>[N:1]1([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([C:20](=[O:22])[CH3:21])[CH:14]=[CH:13]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 3

HCID 4837PiperazineHCID 775062-Acetyl-6-methoxynaphthaleneHCID 3028194Lithium2×

Produkt 1

HCID 153986711-[6-(Piperazin-1-yl)naphthalen-2-yl]ethan-1-one

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5d1a906cbae343b1a09df9fd58202f04
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06274119B1

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