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

HRID 431435

반응식

HRID 431435 반응식
[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

참가 물질

4

반응물 3

HCID 4837PiperazineHCID 775062-Acetyl-6-methoxynaphthaleneHCID 3028194Lithium2회

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-deaa9b0a4aae4aa296572d54c6a593c7
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660530B2

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