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

HRID 565626
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 565626
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.[NH:17]1[CH2:22][CH2:21][CH:20]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[CH2:19][CH2:18]1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[CH3:16][C:3]1([CH2:2][N:26]2[CH2:27][CH2:28][CH:23]([C:20]3[CH:19]=[CH:18][N:17]=[CH:22][CH:21]=3)[CH2:24][CH2:25]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
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 11395974-(4-Piperidyl)pyridineHCID 108505902-Bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine

Produkt 1

HCID 221111302,3-Dihydro-2,4,6,7-tetramethyl-2-[[4-(4-pyridyl)-1-piperidinyl]methyl]-5-benzofuranamineAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

In an autoclave, a mixture of 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine (0.85 g), 4-(4-piperidinyl)pyridine (0.97 g), and triethylamine (1.3 mL) was stirred under nitrogen gas at 180° C. for 15 hours. To this reaction mixture were added saturated aqueous NaHCO3 and ethyl acetate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The pooled organic layer was washed with water and saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=20.1) and crystallized from ethyl acetate/hexane to provide 0.77 g of the title compound. Yield 70%.

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe pooled organic layer was washed with water and saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=20.1)
  8. customcrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-cddf410d28a64f05aacf418c04287ccf
Quelldatensatz
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06172085B2

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