Hydrochloric Acid → Asenapine

HRID 253744

Reaktionsgleichung

Reaktionsgleichung von HRID 253744
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[O:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[C@@H:19]([CH2:27][NH:28][CH3:29])[C@H:18]([C:30](O)=O)[C:17]=2[CH:33]=1.Cl>C1COCC1>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[O:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[C@H:19]3[CH2:27][N:28]([CH3:29])[CH2:30][C@@H:18]3[C:17]=2[CH:33]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 54751968Dibenz[b,f]oxepin-10-carboxylic acid, 8-chloro-10,11-dihydro-11-[(methylamino)methyl]-, hydrochloride (1:1), (10R,11R)-rel-

Produkt 1

HCID 163091Asenapine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a first reaction vessel containing tetrahydrofuran (2.4 mL) at 0° C. was added aluminum chloride (167 mg, 1.26 mmol). To the resulting suspension was slowly added lithium aluminum hydride (3.77 mmol). To a second reaction vessel containing THF (4 mL) was added trans-8-chloro-10,11-dihydro-11-[(methylamino)methyl]-dibenz[b,f]oxepin-10-carboxylic acid hydrochloride (1).HCl (0.4 g, 1.26 mmol). At −10° C., the contents of the first reaction vessel were added to the second reaction vessel. After 30 minutes the reaction mixture was quenched with water and extracted with toluene. The toluene was dried with magnesium sulfate and evaporated. This provided crude trans-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]-oxepino[4,5-c]pyrrole (A) in nearly quantitative yield with a purity of 63%; 1H-NMR (400.13 MHz in CDCl3 relative to TMS) δ 2.54 (s, 3H), 3.15 (m, 2H), 3.25 and 3.61 (2×m, 4H), 7.01-7.36 (m, 7H).

Aufarbeitung

  1. additionAt −10° C., the contents of the first reaction vessel were added to the second reaction vessel
  2. customAfter 30 minutes the reaction mixture was quenched with water
  3. extractionextracted with toluene
  4. dry with materialThe toluene was dried with magnesium sulfate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e373b78e297c4d51b5742137e2455d9c
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872147B2

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