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

HRID 1391988Notes

Reaction equation

HRID 1391988 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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 m L 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.

Workup

  1. custom7°
  2. dry with materialdried in a vacuum desiccator over KOH-drierite mixture for 3 days)
  3. dissolutionwas dissolved in a mixture
  4. customof dry
  5. dissolutionhas dissolved
  6. additionwas added
  7. customAfter quenching with 300 m L of water, extraction with dichloromethane (3×300 mL)
  8. dry with materialdrying with anhydrous magnesium sulfate, and evaporation
  9. additiona mixture of white and yellow solids
  10. customwas obtained
  11. extractionExtraction with 300 mL of hot methanol

Sources & evidence

ORD record
ord-3caf288e790b497a9997ad881e54b0c5
Source dataset
uspto-grants-2008_03
Patent number
US07341709B2

Reaction notes

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