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Water → 4-(4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(3,6-dihydro-2H-pyran-4-yl)-1,3,5-triazin-2-yl)aniline

HRID 1513475
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1513475
O.[O:2]1[CH2:7][CH:6]=[C:5]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=3)[N:11]=[C:10]([N:23]3[CH:28]4[CH2:29][CH2:30][CH:24]3[CH2:25][O:26][CH2:27]4)[N:9]=2)[CH2:4][CH2:3]1>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[CH:24]12[N:23]([C:10]3[N:9]=[C:8]([C:5]4[CH2:6][CH2:7][O:2][CH2:3][CH:4]=4)[N:13]=[C:12]([C:14]4[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=4)[N:11]=3)[CH:28]([CH2:29][CH2:30]1)[CH2:27][O:26][CH2:25]2
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Komponenten

6

Edukt 2

HCID 962WaterHCID 670219658-(4-(3,6-dihydro-2H-pyran-4-yl)-6-(4-nitrophenyl)-1,3,5-triazin-2-yl)-3-oxa-8-azabicyclo[3.2.1]octane

Produkt 1

HCID 670220624-(4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(3,6-dihydro-2H-pyran-4-yl)-1,3,5-triazin-2-yl)anilineAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysator
HCID 176
Acetic Acid
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A mixture of iron powder (0.071 g, 1.27 mmoles) in acetic acid (2 ml) was heated to 55° C. for 15 minutes. Water (2 ml) was then added and oil bath was turned off. A solution of 8-(4-(3,6-dihydro-2H-pyran-4-yl)-6-(4-nitrophenyl)-1,3,5-triazin-2-yl)-3-oxa-8-azabicyclo[3.2.1]octane (0.100 g, 0.253 mmol) in ethyl acetate (2 ml) was then added to this warm solution over 5 minutes. The mixture was cooled to RT and allowed to stir for 16 hours. The mixture was extracted with ethyl acetate by decantation (4×) into a sep. funnel containing saturated aqueous sodium carbonate. The combined organic extracts were washed with water, brine, dried, and concentrated to provide 4-(4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(3,6-dihydro-2H-pyran-4-yl)-1,3,5-triazin-2-yl)aniline (0.068 g, 74%), which was used in the next step without purification. (M+H) 366.4.

Aufarbeitung

  1. customoil bath was turned off
  2. temperatureThe mixture was cooled to RT
  3. extractionThe mixture was extracted with ethyl acetate by decantation (4×) into a sep
  4. additionfunnel containing saturated aqueous sodium carbonate
  5. washThe combined organic extracts were washed with water, brine
  6. customdried
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7f76ebbd0cbf47289d8aeb27acb545f2
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08217036B2

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