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Tert-butyl (1-benzylpiperidin-4-yl)(2,3-dihydro-(1,4)dioxino(2,3-c)pyridin-7-yl methyl)carbamate → Tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(piperidin-4-yl)carbamate monohydrate

HRID 1804728
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1804728
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:22][C:23]2[N:28]=[CH:27][C:26]3[O:29][CH2:30][CH2:31][O:32][C:25]=3[CH:24]=2)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[C].[Pd]>[OH2:16].[O:32]1[C:25]2[CH:24]=[C:23]([CH2:22][N:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[N:28]=[CH:27][C:26]=2[O:29][CH2:30][CH2:31]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 70846775Tert-butyl (1-benzylpiperidin-4-yl)(2,3-dihydro-(1,4)dioxino(2,3-c)pyridin-7-yl methyl)carbamate

Produkt 1

HCID 86646182Tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)(piperidin-4-yl)carbamate monohydrateAusbeute 121,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 5.9 g of tert-butyl (1-benzylpiperidin-4-yl)(2,3-dihydro-(1,4)dioxino(2,3-c)pyridin-7-yl methyl)carbamate in 30 mL of methanol, 1.2 g of 5% palladium carbon was added, and the mixture was stirred for 7 hours at 60° C. under a hydrogen atmosphere. The mixture was subjected to celite filtration, and 40 mL of ethyl acetate and 30 mL of a 0.5 mol/L sodium hydroxide aqueous solution were added to the filtrate. The organic layer was washed with saturated sodium chloride solution, dried using sodium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was recrystallized from 5 mL of ethyl acetate-15 mL of heptane to give 3.0 g of tert-butyl ((2,3-dihydro-(1,4)dioxino(2,3-c)pyridin-7-yl)methyl)(piperidin-4-yl)carbamate monohydrate as a white powder.

Aufarbeitung

  1. filtrationThe mixture was subjected to celite filtration, and 40 mL of ethyl acetate and 30 mL of a 0.5 mol/L sodium hydroxide aqueous solution
  2. additionwere added to the filtrate
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was recrystallized from 5 mL of ethyl acetate-15 mL of heptane

Quellen und Nachweise

ORD-Eintrag
ord-f19f8f1da26f4f4480677d38630737bd
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08354426B2

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