2-Fluorobenzylamine → 2,2-Diethoxy-N-(2-fluorobenzyl)acetamide

HRID 40686

Reaktionsgleichung

Reaktionsgleichung von HRID 40686
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[CH2:10]([O:12][CH:13]([O:17][CH2:18][CH3:19])[C:14]([O-])=[O:15])[CH3:11].[Na+].O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.C(OCC)(=O)C.O>[CH2:10]([O:12][CH:13]([O:17][CH2:18][CH3:19])[C:14]([NH:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[F:1])=[O:15])[CH3:11]

Komponenten

9

Edukt 5

HCID 666492-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23663712Sodium diethoxyacetate

Produkt 1

HCID 596364612,2-Diethoxy-N-(2-fluorobenzyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Fluorobenzylamine (2.00 g, 16.0 mmol), sodium 2,2-diethoxyacetate (3.26 g, 19.2 mmol), N-hydroxybenzotriazole hydrate (3.67 g, 24.0 mmol) and diisopropylethylamine (4.18 mL, 24.0 mmol) were stirred in DMF (20 mL) at room temperature. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.6 g, 24.0 mmol) was added and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was diluted water and ethyl acetate. The organic phase was washed sequentially with HCl (aq) (1 M), saturated sodium bicarbonate, water and brine, dried over sodium sulfate and concentrated to dryness. The crude material was used directly in the following reaction.

Aufarbeitung

  1. washThe organic phase was washed sequentially with HCl (aq) (1 M), saturated sodium bicarbonate, water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness
  4. customThe crude material was used directly in the following reaction

Quellen und Nachweise

ORD-Eintrag
ord-a3d9951b81a141358391e1e1be6fdcfc
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530468B2

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