Hydrochloric Acid → 1-{2-[4-(3-Trifluoromethylphenyl)piperazin-1-yl]ethyl}-1,5,6,7-tetrahydroindol-4-one

HRID 1835080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1835080
[H-].[Na+].[NH:3]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7](=[O:12])[C:6]=2[CH:5]=[CH:4]1.[H][H].Cl[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[CH2:20][CH2:19]1.Cl>CN(C=O)C>[F:33][C:30]([F:31])([F:32])[C:26]1[CH:25]=[C:24]([N:21]2[CH2:20][CH2:19][N:18]([CH2:17][CH2:16][N:3]3[C:11]4[CH2:10][CH2:9][CH2:8][C:7](=[O:12])[C:6]=4[CH:5]=[CH:4]3)[CH2:23][CH2:22]2)[CH:29]=[CH:28][CH:27]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2802291,5,6,7-Tetrahydro-4H-indol-4-oneHCID 112548451-(2-Chloroethyl)-4-[3-(trifluoromethyl)phenyl]piperazineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 101110251-{2-[4-(3-Trifluoromethylphenyl)piperazin-1-yl]ethyl}-1,5,6,7-tetrahydroindol-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (60% in oil) (85 mg, 2.1 mmol, 1.8 eq.) was added to a 10 ml pear-shaped flask. The solid was rinsed twice with 2 mL hexane to remove oil, then 3 mL anhydrous N,N-dimethylformamide(DMF) was added. 1,5,6,7-Tetrahydroindol-4-one (186.7 mg, 1.38 mmol, 1.159 eq.) was added slowly, with stirring and hydrogen evolved. The walls of the flask were washed with an additional 1 mL of anhydrous DMF. 1-(2-Chloro-ethyl)-4-(3-trifluoromethyl-phenyl)-piperazine (349.00 mg, 1.19 mmol, 1.000 eq) was added as a solution in 2 mL DMF, and the mixture was stirred under nitrogen at 25 C for 8 hours. The resulting mixture was acidified with 1 N HCl to pH 6, and extracted with dichloromethane. The organic layer was washed four times with 25 mL water, dried over sodium sulfate and concentrated in vacuum to an oil which was purified by column chromatography using 5% methanol in dichloromethane as eluant resulting in the title compound as an oil. The oil was dissolved in 5 mL of 50% dichloromethane in hexanes. A solution of 4N HCl in dioxane (200 μL) was added and the mixture stirred for 30 minutes followed by vacuum filtration of the suspension. A white powder of the product HCl salt was recovered.

Aufarbeitung

  1. washThe solid was rinsed twice with 2 mL hexane
  2. customto remove oil
  3. addition3 mL anhydrous N,N-dimethylformamide(DMF) was added
  4. washThe walls of the flask were washed with an additional 1 mL of anhydrous DMF
  5. stirringthe mixture was stirred under nitrogen at 25 C for 8 hours
  6. extractionextracted with dichloromethane
  7. washThe organic layer was washed four times with 25 mL water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuum to an oil which
  10. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-34bb374146bd479c8987e19b1e0094c1
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06770638B2

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