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Dibutyltin oxide → HCID 178489644, Verbindung

HRID 2085461
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2085461
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn](=O)CCCC)CCC.C[Si]([N:44]=[N+:45]=[N-:46])(C)C>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)([C:22]2[CH:23]=[CH:24][C:25]([C:26]3[NH:46][N:45]=[N:44][N:27]=3)=[CH:28][CH:29]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 227299114-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-benzonitrile

Produkt 1

HCID 178489644HCID 178489644, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 4-[1-Benzyl-4-(3-methoxy-phenyl)-piperidin-4-yl]-benzonitrile (0.24 g, 0.63 mmol) in toluene (5 mL) were added dibutyltin oxide (0.025 g, 0.1 mmol) and trimethylsilyl azide (0.15 g, 1.26 mmol). The reaction mixture was heated for 60 hours. The mixture was then cooled to room temperature and concentrated under vacuum. The residue was dissolved in methanol (5 mL) and then concentrated. The residue was partitioned between saturated aqueous sodium bicarbonate solution (5 mL) and ethyl acetate. The aqueous layer was washed with ethyl acetate (3×10 mL). The combined extracts were dried (MgSO4) and concentrated. Purification by flash chromatography with CH2Cl2/MeOH (9:1) afforded 0.19 g (71% yield) of 1-Benzyl-4-(3-methoxy-phenyl)4-[4-(1H-tetrazol-5-yl)-phenyl]-piperidine. 1HNMR (400 MHz, CD3OD) δ 7.95 (d, 2H), 7.44-7.41 (comp, 7H), 7.23-7.18 (m, 1H), 6.90-6.77 (comp, 2H), 6.76 (d, 1H), 6.70 (d, 1H), 4.21 (s, 2H), 3.64 (s, 3H), 3.30-2.41 (comp, 8H); MS (M+1) 426.2.

Aufarbeitung

  1. temperatureThe reaction mixture was heated for 60 hours
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in methanol (5 mL)
  4. concentrationconcentrated
  5. customThe residue was partitioned between saturated aqueous sodium bicarbonate solution (5 mL) and ethyl acetate
  6. washThe aqueous layer was washed with ethyl acetate (3×10 mL)
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. concentrationconcentrated
  9. customPurification by flash chromatography with CH2Cl2/MeOH (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-254f62cad62d4b1ebae947fad282971e
Quelldatensatz
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06720336B2

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