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Sodium hydride → Ethyl 4-[N-cyclopropylmethyl-(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate

HRID 1097397
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1097397
[H-].[Na+].[CH3:3][C:4]12[C:16]3[C:8](=[CH:9][C:10]([NH:17][C:18]4[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=4)=[CH:11][C:12]=3[CH2:13][CH2:14][CH2:15]1)[CH2:7][CH2:6][CH2:5]2.Br[CH2:30][CH:31]1[CH2:33][CH2:32]1.[Cl-].[NH4+]>CN(C)C=O>[CH:31]1([CH2:30][N:17]([C:10]2[CH:9]=[C:8]3[C:16]4[C:4]([CH3:3])([CH2:5][CH2:6][CH2:7]3)[CH2:15][CH2:14][CH2:13][C:12]=4[CH:11]=2)[C:18]2[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:27][CH:28]=2)[CH2:33][CH2:32]1
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Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 81503BromomethylcyclopropaneHCID 25190221Ethyl 4-[(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate

Produkt 1

HCID 25190163Ethyl 4-[N-cyclopropylmethyl-(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A suspension of sodium hydride (60%, 0.013 g) in N,N-dimethylformamide (2 ml) was added with ethyl 4-[(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate (0.055 g) dissolved in N,N-dimethylformamide (2 ml), and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was added with bromomethylcyclopropane (0.035 ml), the mixture was stirred overnight at room temperature, and then added with saturated aqueous ammonium chloride, and the mixture was extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:50) to quantitatively obtain the title compound (0.063 g).

Aufarbeitung

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:50)

Quellen und Nachweise

ORD-Eintrag
ord-7cf59356461a413bb49a74381fcd30a2
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08143260B2

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