Tetrahydrofuran → Morpholino(3-nitrophenyl)methanone

HRID 1261987

Reaktionsgleichung

Reaktionsgleichung von HRID 1261987
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.O1CCCC1.C(=O)(O)[O-].[Na+]>>[N:13]1([C:7]([C:6]2[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[O:9])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Komponenten

7

Edukt 6

HCID 8028TetrahydrofuranHCID 8083MorpholineHCID 84973-Nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 225453Morpholino(3-nitrophenyl)methanoneAusbeute 98,4 %

Versuchsvorschrift

m-Nitrobenzoic acid (2.00 g, 0.0120 mol), Morpholine (1.25 g, 0.0144 mol), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (2.29 g, 0.0120 mol) and 1-Hydroxybenzotriazole (0.40 g, 0.0030 mol) were dissolved in Tetrahydrofuran (35 mL, 0.43 mol) and the reaction was allowed to stir overnight at room temperature. The reaction mixture was poured over saturated sodium bicarbonate, and organics were extracted with ethyl acetate/dichloromethane. Combined organics were dried over sodium sulfate, filtered and reduced en vacuo. The crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate). Combined fractions were reduced en vacuo to afford 2.79 g of Morpholin-4-yl-(3-nitro-phenyl)-methanone. (M+H)=237.5.

Aufarbeitung

  1. extractionorganics were extracted with ethyl acetate/dichloromethane
  2. dry with materialCombined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customThe crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1ea538fb473f4490b0bd3f1e33c1c298
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471005B2

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