Hydrochloric Acid → Dibenz[b,f]oxepin-10-carboxylic acid, 8-chloro-10,11-dihydro-11-[(methylamino)methyl]-, hydrochloride (1:1), (10R,11R)-rel-

HRID 1970100Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1970100
Cl.C(OCC)(=[O:4])C.[Cl:8][C:9]1[CH:28]=[CH:27][C:12]2[O:13][C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C@H:16]3[CH2:20][N:19]([CH3:21])[C:18](=[O:22])[C@@H:17]3[C:11]=2[CH:10]=1>C1(C)C(C)=CC=CC=1>[ClH:8].[Cl:8][C:9]1[CH:28]=[CH:27][C:12]2[O:13][C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C@@H:16]([CH2:20][NH:19][CH3:21])[C@H:17]([C:18]([OH:22])=[O:4])[C:11]=2[CH:10]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 54753299Trans-(+-)-11-chloro-2,3,3a,12b-tetrahydro-2-methyl-1h-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one

Produkt 1

HCID 54751968Dibenz[b,f]oxepin-10-carboxylic acid, 8-chloro-10,11-dihydro-11-[(methylamino)methyl]-, hydrochloride (1:1), (10R,11R)-rel-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

HCl (55.5 g) and silica gel (55 g) were suspended in xylene (550 mL). The suspension was heated to reflux for 1 night. The reaction mixture was cooled to 65° C. and ethyl acetate (550 mL) was added. The silica gel was filtered off and washed with ethyl acetate (550 mL). The organic phase was evaporated. The crude product was dissolved in methanol (750 mL). The methanol was partly evaporated upon which crystallization of the product takes place. After cooling to 5° C. for 3 hours, the product was obtained by filtration. This yielded trans-11-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (IV) (47.8 g, 86%); mp 150.6° C.; 1H-NMR (400.13 MHz in CDCl3 relative to TMS) δ 3.03 (d, 3H), 4.03 (m, 1H), 3.53-3.65 (m, 2H), 3.82 (m, 1H), 7.01-7.28 (m, 6H), 7.87 (dd, 1H).

Aufarbeitung

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 1 night
  3. filtrationThe silica gel was filtered off
  4. washwashed with ethyl acetate (550 mL)
  5. customThe organic phase was evaporated
  6. dissolutionThe crude product was dissolved in methanol (750 mL)
  7. customThe methanol was partly evaporated upon which crystallization of the product
  8. temperatureAfter cooling to 5° C. for 3 hours
  9. customthe product was obtained by filtration

Quellen und Nachweise

ORD-Eintrag
ord-3ddd77fae85b4e359dafee3d94a1b1e8
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426610B2

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