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1,3-Dibromopropane → 7-(Azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1044523
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1044523
[NH2:1][CH:2]1[CH:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2[CH:9]=[C:8]([C:19]#[N:20])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.Br[CH2:22][CH2:23][CH2:24]Br.C(N(CC)CC)C>C(#N)C>[N:1]1([CH:2]2[CH:11]([CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:10]3[CH:9]=[C:8]([C:19]#[N:20])[CH:7]=[CH:6][C:5]=3[CH2:4][CH2:3]2)[CH2:24][CH2:23][CH2:22]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 80011,3-DibromopropaneHCID 8471TriethylamineHCID 57471403HCID 57471403, Verbindung

Produkt 1

HCID 574714047-(Azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

7-Amino-8-benzyl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (790 mg, 3.03 mmol), 1,3-dibromopropane (0.4 mL, 3.93 mmol) and triethylamine (0.914 mL, 6.56 mmol) were dissolved in acetonitrile (8 mL) and the reaction mixture heated to 120° C. in the microwave for 2 h. The solvent was evaporated in vacuo. Water (30 mL) and ethyl acetate (40 mL) were added. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and the solvent evaporated in vacuo. The crude product was purified by flash chromatography (silica gel, dichloromethane, methanol). Yield: 346 mg (1.14 mmol, 37.6%).

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. additionWater (30 mL) and ethyl acetate (40 mL) were added
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customthe solvent evaporated in vacuo
  7. customThe crude product was purified by flash chromatography (silica gel, dichloromethane, methanol)

Quellen und Nachweise

ORD-Eintrag
ord-8eae3ba9a4f647eb968cd773baa66ae4
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08563617B2

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