1-(1-Naphthyl)piperazine → 6-(4-(4-(1-Naphthyl)piperazinyl)butyl)-benzoxazolone

HRID 365366Notes

Reaction equation

HRID 365366 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]2[NH:10][C:11](=[O:13])[O:12][C:8]=2[CH:7]=1.[C:16]1([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>[I-].[Na+].C(O)(C)C>[C:16]1([N:26]2[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]3[CH:15]=[CH:14][C:9]4[NH:10][C:11](=[O:13])[O:12][C:8]=4[CH:7]=3)[CH2:28][CH2:27]2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 13421-(1-Naphthyl)piperazineHCID 10340Sodium CarbonateHCID 14581391HCID 14581391, compound

Product 1

HCID 112925496-(4-(4-(1-Naphthyl)piperazinyl)butyl)-benzoxazoloneYield 543.1%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 3776IsopropanolSolvent

Procedure

To a 100 ml round-bottom flask equipped with condenser and nitrogen inlet were added 0.658 grams (3.10 mmol) of 6-(4-chlorobutyl)-benzoxazolone, 0.7 grams (3.10 mmol) of N-(1-naphthyl)piperazine, 0.328 grams sodium carbonate, 2 mg sodium iodide, and 50 ml isopropanol. The reaction was refluxed for 3 days, evaporated, taken up in methylene chloride, washed with water, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using ethyl acetate as eluent, and the product dissolved in acetone, precipitated with ethereal HCl, and the white solid filtered, washed with acetone, and dried to afford 6.76 grams (46.0%) of a white solid, m.p. 231°-233° C.

Workup

  1. customTo a 100 ml round-bottom flask equipped with condenser and nitrogen inlet
  2. temperatureThe reaction was refluxed for 3 days
  3. customevaporated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. dissolutionthe product dissolved in acetone
  9. customprecipitated with ethereal HCl
  10. filtrationthe white solid filtered
  11. washwashed with acetone
  12. customdried

Sources & evidence

ORD record
ord-ea11aa3fe9954ed29a9aeb0a227dfaef
Source dataset
uspto-grants-2000_10
Patent number
US06127373

Reaction notes

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