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Carbon Dioxide → 1-[2-(4-Hydroxyphenylamino)benzoyl]piperidine

HRID 464789
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 464789
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[CH:27]=[CH:26][CH:25]=[CH:24][C:15]=2[C:16]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])=[CH:9][CH:8]=1.C(=O)=O.C(O)(C)C>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14]2[CH:27]=[CH:26][CH:25]=[CH:24][C:15]=2[C:16]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])=[CH:11][CH:12]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 280Carbon DioxideHCID 3776IsopropanolHCID 25134Boron tribromideHCID 135056301-[2-(4-Methoxyphenylamino)benzoyl]piperidine

Produkt 1

HCID 135056311-[2-(4-Hydroxyphenylamino)benzoyl]piperidineAusbeute 68,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

Boron tribromide (10 ml in 25 ml of methylene dichloride) was added dropwise over a 30 minute period to a solution of 15.5 g of 1-[2-(4-methoxyphenylamino)benzoyl]piperidine in 80 ml of dry methylene dichloride cooled in a bath of Dry Ice and isopropyl alcohol. The reaction mixture was allowed to warm to room temperature and to stand overnight. The solvent was then removed in vacuo, and the residue was treated with 100 ml of distilled water and made basic with about 250 ml of saturated sodium bicarbonate solution. The solid which formed was collected by filtration and recrystallized from ethanol to give 10.2 g of 1-[2-(4-hydroxyphenylamino)benzoyl]piperidine, colorless powder, m.p. 199°-201° C. (decompn.).

Aufarbeitung

  1. customThe solvent was then removed in vacuo
  2. additionthe residue was treated with 100 ml of distilled water
  3. customThe solid which formed
  4. filtrationwas collected by filtration
  5. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-7693cbdf245f4970af51fe0ce63014f4
Quelldatensatz
uspto-grants-1985_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04549016

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