Sodium Iodide → 1-[4-Cyano-5-methyl-4-(2-naphthyl)hexyl]-4-[2-(4-fluorophenoxy)ethyl]piperazine

HRID 1071646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071646
[C:1]([C:3]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:5][CH2:6]O)#[N:2].C(N(CC)CC)C.S(Cl)(C)(=O)=O.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[F:41][C:42]1[CH:56]=[CH:55][C:45]([O:46][CH2:47][CH2:48][N:49]2[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]2)=[CH:44][CH:43]=1>C(#N)C.[Cl-].[Na+].O.O.CN(C)C=O>[C:1]([C:3]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)([CH:8]([CH3:9])[CH3:10])[CH2:4][CH2:5][CH2:6][N:52]1[CH2:53][CH2:54][N:49]([CH2:48][CH2:47][O:46][C:45]2[CH:44]=[CH:43][C:42]([F:41])=[CH:56][CH:55]=2)[CH2:50][CH2:51]1)#[N:2]

Komponenten

11

Edukt 6

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 8950271-[2-(4-Fluorophenoxy)ethyl]piperazineHCID 223937754-Cyano-5-methyl-4-(2-naphthyl)hexanol

Produkt 1

HCID 223936531-[4-Cyano-5-methyl-4-(2-naphthyl)hexyl]-4-[2-(4-fluorophenoxy)ethyl]piperazineAusbeute 69,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

In acetonitrile (5 ml) was dissolved 310 mg (1.16 mmol) of 4-cyano-5-methyl-4-(2-naphthyl)hexanol, followed by adding 190 μL (1.36 mmol) of triethylamine and 105 μl (1.36 mmol) of mesyl chloride. After completion of mesylation, 1.11 g (7.38 mmol) of sodium iodide, 255 mg (1.85 mmol) of potassium carbonate, 414 mg (1.85 mmol) of 1-[2-(4-fluorophenoxy) ethyl]piperazine, 5 ml of dimethylformamide and 1 ml of water were added thereto, followed by heating to 60° C. After completion of the reaction, brine was added thereto and the objective product was extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, to give a crude product. The crude product was subjected to (NH) silica gel (eluted with ethyl acetate/hexane=2/3), to give 384 mg (0.81 mmol, 69.9%) of the title compound as a yellow syrup.

Aufarbeitung

  1. additionwas added
  2. extractionthe objective product was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customto give a crude product

Quellen und Nachweise

ORD-Eintrag
ord-e76a4419ea6b47f2a9c8a9df2889489b
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06906072B1

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