1-(1-Naphthyl)piperazine → HCID 14727016, compound

HRID 329406Notes

Reaction equation

HRID 329406 reaction equation
Br.Cl[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([NH:18]C)[S:16][CH:17]=2)=[CH:9][CH:8]=1.[C:20]1([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(OCC)(=O)C.CC(CC(C)C)=O>[C:20]1([N:30]2[CH2:35][CH2:34][N:33]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]3[CH:8]=[CH:9][C:10]([C:13]4[N:14]=[C:15]([NH2:18])[S:16][CH:17]=4)=[CH:11][CH:12]=3)[CH2:32][CH2:31]2)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 13421-(1-Naphthyl)piperazineHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 19872079HCID 19872079, compound

Product 1

HCID 14727016HCID 14727016, compound

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 125 ml round-bottomed flask equipped with condenser and N2 inlet were added 2.61 g (7.5 mmol) of 4-(4-(4-chlorobutyl)phenyl)-2-methylaminothiazole hydrobromide, 1.59 g (7.5 mmol) of N-(1-naphthyl)piperazine, 1.31 ml (7.5 mmol) of diisopropyethylamine, 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 4.5 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 ethyl acetate, precipitated by addition of ethyl acetate saturated with hydrochloride, and the precipitate filtered, washed with ethyl acetate, and dried to give a white solid, m.p. 242°-245° C., 1.67 g (43%).

Workup

  1. customTo a 125 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 4.5 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 ethyl acetate saturated with hydrochloride
  10. filtrationthe precipitate filtered
  11. washwashed with ethyl acetate
  12. customdried
  13. customto give a white solid, m.p. 242°-245° C., 1.67 g (43%)

Sources & evidence

ORD record
ord-54e599382b67493dabedf6f82bb0a3b5
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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