Sodium Hydroxide → HCID 53794087, Verbindung

HRID 894467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 894467
Cl[C:2]1[C:19]([O:20][CH3:21])=[CH:18][C:5]2[C@H:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:7][N:8]([CH3:11])[CH2:9][CH2:10][C:4]=2[CH:3]=1.[OH-].[Na+].[H][H]>C(O)C.O.[Pd]>[CH3:21][O:20][C:19]1[CH:2]=[CH:3][C:4]2[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][C@@H:6]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:5]=2[CH:18]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 12928524HCID 12928524, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 53794087HCID 53794087, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23219155Palladium hydrateKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Hydrogenate a solution of 21.10 g (0.07 moles) of (S)-7-chloro-8-methoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1-H-3-benzazepine (e.g. obtained as described in Example 1, step D) 3.30 g (0.0825 moles) of sodium hydroxide in 300 ml of 95% ethanol at room temperature and at 4.2 kg/cm2 (=60 psi), with 1.70 g of 20% palladium hydroxide-on-carbon until the theoretical amount of hydrogen is consumed. Remove the catalyst and concentrate the filtrate to dryness on a steam bath at about 100 mm. Stir the residue with a mixture of 100 ml of water and 150 ml of ethyl ether to total dissolution. Separate the ether layer, dry over anhydrous sodium sulfate, and evaporate to dryness. Crystallize the residue from hexane to obtain analytically pure (S)-8-methoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine, m.p. 50°-51° C., [α]D26 =+51.8° (c=1, ethanol).

Aufarbeitung

  1. customRemove the catalyst
  2. concentrationconcentrate the filtrate to dryness on a steam bath at about 100 mm
  3. additionwith a mixture of 100 ml of water and 150 ml of ethyl ether
  4. dissolutiondissolution
  5. customSeparate the ether layer
  6. dry with materialdry over anhydrous sodium sulfate
  7. customevaporate to dryness
  8. customCrystallize the residue from hexane

Quellen und Nachweise

ORD-Eintrag
ord-f21867134f084352828f2449a19e630e
Quelldatensatz
uspto-grants-1981_08
Patentnummer
US04284555

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