Reaktion #1621767

Reaktionsgleichung

NaOH

5-Methoxy-8-chloro-11-(1-methyl-4-piperidinyl)-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol

H2SO4

→

8-chloro-11-hydroxy-11-(1-methyl-4-piperidinyl)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-5-one

HCl

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONPour the solution onto ice
2. 2
   Extraktionextract with methylene chloride (3×)
3. 3
   WaschenCombine the organic portions, wash with brine
4. 4
   Trocknendry over sodium sulfate
5. 5
   FiltrationFilter
6. 6
   Einengenconcentrate in vacuo
7. 7
   SonstigeTriturate the residue with isopropyl ether

Vorschrift

Dissolve 5-Methoxy-8-chloro-11-(1-methyl-4-piperidinyl)-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol (4.26 g) in CH30H (6 mL) at 0° C. under an argon atmosphere. Add slowly a cooled solution of 92% aqueous H2SO4 (54 mL). Allow the mixture to warm to room temperature for 35 minutes. Pour the solution onto ice, basify with aqueous NaOH (25%), and extract with methylene chloride (3×). Combine the organic portions, wash with brine and dry over sodium sulfate. Filter and concentrate in vacuo. Triturate the residue with isopropyl ether to give an intermediate, 8-chloro-11-hydroxy-11-(1-methyl-4-piperidinyl)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-5-one as a white solid (3.58 g., 92%, m.p. 170° to 174° C. as HCl salt).

Quelle