Triethylamine → 2,3-Dihydro-2,4,6,7-tetramethyl-2-[[4-(2-phenylethyl)-1-piperidinyl]methyl]-5-benzofuranamine

HRID 565686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 565686
Br[CH2:2][C:3]1([CH3:16])[CH2:7][C:6]2[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.[C:17]1([CH2:23][CH2:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>C([O-])(O)=O.[Na+]>[CH3:16][C:3]1([CH2:2][N:28]2[CH2:29][CH2:30][CH:25]([CH2:24][CH2:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:26][CH2:27]2)[CH2:7][C:6]2[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 43418954-(2-Phenylethyl)piperidineHCID 108505902-Bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine

Produkt 1

HCID 154858772,3-Dihydro-2,4,6,7-tetramethyl-2-[[4-(2-phenylethyl)-1-piperidinyl]methyl]-5-benzofuranamineAusbeute 42,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

In an autoclave, a mixture of 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine (1.5 g), 4-(2-phenylethyl)piperidine (2.0 g), and triethylamine (5.3 g) was stirred under argon gas at 180° C. for 15 hours. After cooling, the reaction mixture was diluted with saturated aqueous NaHCO3 and extracted with ethyl acetate. The extract was washed with saturated aqueous NaCl and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:1) and recrystallized from diisopropyl ether to provide 0.88 g of the title compound. Yield 42%.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:1)
  7. customrecrystallized from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-48191aeed5bb4d0e9fa03d8a3961a655
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172085B2

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