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Sodium Hydroxide → 5H-Dibenz(b,f)azepine, 8-chloro-10-(2-(dimethylamino)ethyl)-5-methyl-

HRID 1576246
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1576246
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[N:12]([CH3:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:22]O)([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[C:4]=2[CH:3]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[N:12]([CH3:16])[C:11]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[CH:22]=[C:5]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[C:4]=2[CH:3]=1
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Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 12813968HCID 12813968, Verbindung

Produkt 1

HCID 2076745H-Dibenz(b,f)azepine, 8-chloro-10-(2-(dimethylamino)ethyl)-5-methyl-Ausbeute 82,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture of 5 gm of 2-chloro-9-hydroxymethyl-9-(β-dimethylaminoethyl)-10-methyl-acridane, 150 cc of xylene and 25 gm of phosphoric acid anhydride was refluxed for 3 hours under a nitrogen atmosphere and after cooling, the reaction mixture was poured into a water-ice mixture. The mixture was made alkaline by the addition of 35 cc sodium hydroxide solution and was extracted with ethyl acetate. The organic phase was washed with an aqueous sodium chloride solution, dried over magnesium sulfate, treated with charcoal, filtered and evaporated to dryness to obtain 3.9 gm of raw 8-chloro-5-methyl-10-(β-dimethylaminoethyl)dibenzo (b,f) azepine. The 3.9 gm of raw product were dissolved in 15 cc of methanol and a solution of 1.2 gm of fumaric acid in 45 cc of methanol was added thereto. The methanol was distilled off and replaced with ethyl acetate and the mixture was then refrigerated for 48 hours for crystallization and filtered. The precipitate was washed with ethyl acetate and dried to obtain 2.8 gm, the fumarate of 8-chloro-5-methyl-10-(β-dimethylaminoethyl)-dibenzo (b,f) azepine melting at 150°C, then 164°C. Cooling of the mother liquors gave a second crop of 0.25 g of product.

Aufarbeitung

  1. temperaturewas refluxed for 3 hours under a nitrogen atmosphere
  2. temperatureafter cooling
  3. extractionwas extracted with ethyl acetate
  4. washThe organic phase was washed with an aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with charcoal
  7. filtrationfiltered
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-d2ae55b8cf2f49f398a7557905fb6db8
Quelldatensatz
uspto-grants-1976_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03979515

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