1-(1-Naphthyl)piperazine → 4-{4-[2-(4-Naphthalen-1-yl-piperazin-1-yl)-ethyl]-phenyl}-thiazol-2-ol

HRID 329399Notes

Reaction equation

HRID 329399 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][C:12](=[O:15])[S:13][CH:14]=2)=[CH:6][CH:5]=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(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>[I-].[Na+].CC(CC(C)C)=O>[C:16]1([N:26]2[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][C:7]([C:10]4[NH:11][C:12](=[O:15])[S:13][CH:14]=4)=[CH:6][CH:5]=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

7

Reactant 4

HCID 13421-(1-Naphthyl)piperazineHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 150542144-(4-(2-Chloroethyl)phenyl)thiazol-2-one

Product 1

HCID 150542154-{4-[2-(4-Naphthalen-1-yl-piperazin-1-yl)-ethyl]-phenyl}-thiazol-2-olYield 21.6%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a 35 ml round-bottomed flask equipped with condenser and N2 inlet were added 1.40 g (5.84 mmol) of 4-(4-(2-chloroethyl)phenyl)thiazol-2-one, 1.24 g (5.84 mmol) of N-(1-naphthyl)piperazine, 0.81 ml (5.84 mmol) of triethylamine, 0.62 g (5.84 mmol) of sodium carbonate, 2 mg of sodium iodide, and 12 ml of methylisobutylketone. The reaction was heated at reflux for 5 days, cooled, and evaporated. The residue was taken up in ethyl acetate/water, the layers separated, and the ethyl acetate layer washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using ethyl acetate/methylene chloride as eluent. The product fractions were evaporated, and the residue taken up in hot methylene chloride/methanol, treated with ethyl acetate saturated with hydrochloride, precipitated with ether, filtered, washed with ether, and dried to give 0.523 g (18%) of a white solid, m.p. 307°-309° C.

Workup

  1. customTo a 35 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 5 days
  4. temperaturecooled
  5. customevaporated
  6. customthe layers separated
  7. washthe ethyl acetate layer washed with brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customThe residue was chromatographed on silica gel
  11. customThe product fractions were evaporated
  12. additiontreated with ethyl acetate saturated with hydrochloride
  13. customprecipitated with ether
  14. filtrationfiltered
  15. washwashed with ether
  16. customdried

Sources & evidence

ORD record
ord-35c1a864d3c74004b8e8b698bf0e361e
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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