1-(1-Naphthyl)piperazine → 1-{2-[4-(2-Methyl-thiazol-4-yl)-phenyl]-ethyl}-4-naphthalen-1-yl-piperazine

HRID 329403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 329403
Br.Cl[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([CH3:16])[S:14][CH:15]=2)=[CH:7][CH:6]=1.[C:17]1([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CC(CC(C)C)=O>[C:17]1([N:27]2[CH2:32][CH2:31][N:30]([CH2:3][CH2:4][C:5]3[CH:10]=[CH:9][C:8]([C:11]4[N:12]=[C:13]([CH3:16])[S:14][CH:15]=4)=[CH:7][CH:6]=3)[CH2:29][CH2:28]2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

Komponenten

7

Edukt 5

HCID 13421-(1-Naphthyl)piperazineHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 147269914-(4-(2-Chloroethyl)phenyl)-2-methylthiazole hydrobromide

Produkt 1

HCID 147270121-{2-[4-(2-Methyl-thiazol-4-yl)-phenyl]-ethyl}-4-naphthalen-1-yl-piperazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

To a 125 ml round-bottomed flask equipped with condenser and N2 inlet were added 2.39 g (7.5 mmol) of 4-(4-(2-chloroethyl)phenyl)-2-methylthiazole 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 5 days, cooled, and the precipitate filtered. The solid was taken up in methylene chloride, washed with sodium bicarbonate, dried over sodium sulfate, treated with methylene chloride saturated with hydrochloride, evaporated, and the residue triturated with ether to afford a white solid, m.p. 305°-307° C., 1.76 g (48%).

Aufarbeitung

  1. customTo a 125 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 5 days
  4. temperaturecooled
  5. filtrationthe precipitate filtered
  6. washwashed with sodium bicarbonate
  7. dry with materialdried over sodium sulfate
  8. additiontreated with methylene chloride saturated with hydrochloride
  9. customevaporated
  10. customthe residue triturated with ether
  11. customto afford a white solid, m.p. 305°-307° C., 1.76 g (48%)

Quellen und Nachweise

ORD-Eintrag
ord-82d4d90b35544a80aca467bfe97325ee
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04891375

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