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Sodium hydride → (r)-5,11-Dihydro-5-[1-(3-methoxyphenethyl)piperidine-2-ylmethyl] dibenzo[b,e][1,4]oxazepine

HRID 1859426
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1859426
[H-].[Na+].[CH:3]1[C:13]2[CH2:12][O:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl[C@@H:19]1[CH2:25][CH2:24][CH2:23][CH2:22][N:21]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=2)[CH2:20]1>CCCCCC.CS(C)=O.C(=O)([O-])O.[Na+].C(OCC)(=O)C>[CH3:35][O:34][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][CH:31]=1)[CH2:27][CH2:26][N:21]1[CH2:22][CH2:23][CH2:24][CH2:25][C@@H:20]1[CH2:19][N:8]1[C:7]2[CH:6]=[CH:5][CH:4]=[CH:3][C:13]=2[CH2:12][O:11][C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]1=2
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Komponenten

8

Edukt 3

HCID 24758Sodium hydrideHCID 110847985,11-Dihydrodibenzo[b,e][1,4]oxazepineHCID 22975049(R)-3-chloro-1-(3-methoxyphenethyl)homopiperidine

Produkt 1

HCID 12018617(r)-5,11-Dihydro-5-[1-(3-methoxyphenethyl)piperidine-2-ylmethyl] dibenzo[b,e][1,4]oxazepine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 679Dimethyl Sulfoxide
Lösungsmittel
2×
HCID 8058HexaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel
HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

60% Sodium hydride (27 mg, 0.68 mmol) was washed with hexane under argon atmosphere, and then suspended in dimethyl sulfoxide (5 ml). The obtained suspension was stirred at room temperature for 30 minutes. 5,11-Dihydrodibenzo[b,e][1,4]oxazepine (122 mg, 0.68 mmol) was added to the suspension, and they were stirred at room temperature for 20 minutes and then at 50° C. for 30 minutes. A solution of (R)-3-chloro-1-(3-methoxyphenethyl)homopiperidine (182 mg, 0.68 mmol) in dimethyl sulfoxide (3 ml) was added dropwise into the obtained solution, and they were stirred at 50° C. for 150 minutes. The reaction liquid was distributed in saturated aqueous sodium hydrogencarbonate solution and ethyl acetate. The organic layer was dried, and the solvent was evaporated under reduce pressure. The obtained residue was subjected to silica gel column chromatography. The product was eluted with hexane and ethyl acetate (10:1) and then with hexane and ethyl acetate (4:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (R)-5,11-dihydro-5-[1-(3-methoxyphenethyl)piperidine-2-ylmethyl] dibenzo[b,e][1,4]oxazepine in the form of a light yellow oil (78 mg, 30%).

Aufarbeitung

  1. stirringwere stirred at room temperature for 20 minutes
  2. waitat 50° C. for 30 minutes
  3. stirringwere stirred at 50° C. for 150 minutes
  4. customThe reaction liquid
  5. customThe organic layer was dried
  6. customthe solvent was evaporated
  7. washThe product was eluted with hexane and ethyl acetate (10:1)
  8. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2622a7a3870f470e8389dfed61972e07
Quelldatensatz
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06528504B2

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