Hydrochloric Acid → 5-(2-hydroxyethoxy)-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

HRID 54752

Reaktionsgleichung

Reaktionsgleichung von HRID 54752
[BH4-].[Li+].C([O:5][C:6]([CH2:8][O:9][CH:10]1[C:16]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=2[N:14]([C:22](=[O:39])[C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:38])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH3:37])=[CH:25][CH:24]=2)[CH2:13][CH2:12][CH2:11]1)=O)C.Cl>O1CCCC1>[OH:5][CH2:6][CH2:8][O:9][CH:10]1[C:16]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=2[N:14]([C:22](=[O:39])[C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:38])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[CH3:37])=[CH:25][CH:24]=2)[CH2:13][CH2:12][CH2:11]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 189173325-ethoxycarbonylmethoxy-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

Produkt 1

HCID 189174515-(2-hydroxyethoxy)-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepineAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

0.28 g of lithium borohydride was added to a solution of 2.2 g of 5-ethoxycarbonylmethoxy-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzo-azepine dissolved in 50 ml of tetrahydrofuran, at room temperature with stirring. The mixture was refluxed for 30 minutes. The reaction mixture was poured into a diluted hydrochloric acid. The mixture was subjected to extraction with dichloromethane. The extract was dried over magnesium sulfate and subjected to vacuum distillation to remove the solvent. The residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol=100/1→50/1) and then recrystallized from dichloromethane-diethyl ether to obtain 1.6 g of 5-(2-hydroxyethoxy)-7-chloro-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 30 minutes
  2. extractionThe mixture was subjected to extraction with dichloromethane
  3. dry with materialThe extract was dried over magnesium sulfate
  4. distillationsubjected to vacuum distillation
  5. customto remove the solvent
  6. customThe residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol=100/1→50/1)
  7. customrecrystallized from dichloromethane-diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-7746469717dd40258fff531d5fb7e20e
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622947

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