1-(1-Naphthyl)piperazine → HCID 14727008, compound

HRID 329402Notes

Reaction equation

HRID 329402 reaction equation
Br.Cl[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([NH:16][CH3:17])[S:14][CH:15]=2)=[CH:7][CH:6]=1.[C:18]1([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(Cl)Cl.CC(CC(C)C)=O>[C:18]1([N:28]2[CH2:33][CH2:32][N:31]([CH2:3][CH2:4][C:5]3[CH:10]=[CH:9][C:8]([C:11]4[N:12]=[C:13]([NH:16][CH3:17])[S:14][CH:15]=4)=[CH:7][CH:6]=3)[CH2:30][CH2:29]2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 5

HCID 13421-(1-Naphthyl)piperazineHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 14726987HCID 14726987, compound

Product 1

HCID 14727008HCID 14727008, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a 125 ml round-bottomed flask equipped with condenser and N2 inlet were added 2.50 g (7.5 mmol) of 4-(4-(2-chloroethyl)phenyl)-2-methylaminothiazole hydrobromide, 1.59 g (7.5 mmol) of N-(1-naphthyl)piperazine, 1.31 ml (7.5 mmol) of diisopropylethylamine, 1.59 g (15 mmol) of sodium carbonate, 5 mg of sodium iodide, and 50 ml of methylisobutylketone. The reaction was heated at reflux for 4 days, cooled, and the precipitate filtered, and the filtrate evaporated. The residue was taken up in methylene chloride and chromatographed on silica gel using methylene chloride/ethyl acetate as eluent to give an oil. The oil was taken up in methylene chloride, precipitated by addition of methylene chloride saturated with hydrochloride, and the precipitate filtered, washed with ether, and dried to give a white solid, m.p. 272°-273° C., 2.37 g (63%).

Workup

  1. customTo a 125 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 4 days
  4. temperaturecooled
  5. filtrationthe precipitate filtered
  6. customthe filtrate evaporated
  7. customchromatographed on silica gel
  8. customto give an oil
  9. customprecipitated by addition of methylene chloride saturated with hydrochloride
  10. filtrationthe precipitate filtered
  11. washwashed with ether
  12. customdried
  13. customto give a white solid, m.p. 272°-273° C., 2.37 g (63%)

Sources & evidence

ORD record
ord-f36e3fc9d03147d98d3252b1eaf16f60
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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