Lithium iodide → (cis)-7-chloro-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-3-methyl-2H-1-benzazepin-2-one

HRID 580383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 580383
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[C:9](C(OC)=O)([CH3:13])[CH:8]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH2:7][C:6]=2[CH:26]=1.[I-].[Li+]>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[C@@H:9]([CH3:13])[C@@H:8]([C:18]3[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=3)[CH2:7][C:6]=2[CH:26]=1

Komponenten

5

Edukt 2

HCID 66321Lithium iodideHCID 15128679HCID 15128679, Verbindung

Produkt 1

HCID 67866507(cis)-7-chloro-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-3-methyl-2H-1-benzazepin-2-oneAusbeute 58,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 800 mg of 7-chloro-1,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-3-methyl-2H-1-benzazepin-2-one (2.16 mmole), 1.14 g of lithium iodide (8.56 mmoles, 4 equiv.) in 20 ml of pyridine was refluxed for 20 hours. The cooled mixture was diluted with 200 ml of ethyl acetate, then washed with four 30 ml portions of 1N hydrochloric acid, two 30 ml portions of saturated cupric sulfate, 30 ml of water. The organic layer was dried (magnesium sulfate) and concentrated. The residue was triturated with ether to yield 400 mg of (cis)-7-chloro-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-3-methyl-2H-1-benzazepin-2-one as a white solid.

Aufarbeitung

  1. temperaturewas refluxed for 20 hours
  2. washwashed with four 30 ml portions of 1N hydrochloric acid, two 30 ml portions of saturated cupric sulfate, 30 ml of water
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. concentrationconcentrated
  5. customThe residue was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-2881c2fd43384e62af52915f5c5f2167
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04752645

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