Water → N-methoxy-N-methyl-2-phenylbutanamide

HRID 2118210

Reaktionsgleichung

Reaktionsgleichung von HRID 2118210
N1C=CC=CC=1.Cl.[CH3:8][NH:9][O:10][CH3:11].[C:12]1([CH:18]([CH2:22][CH3:23])[C:19](Cl)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>C(Cl)Cl.C1COCC1>[CH3:11][O:10][N:9]([CH3:8])[C:19](=[O:20])[CH:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:22][CH3:23]

Komponenten

7

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 981732-Phenylbutyryl chloride

Produkt 1

HCID 11229537N-methoxy-N-methyl-2-phenylbutanamideAusbeute 979,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of pyridine (33.1 mL, 40.9 mmol) and N,O-dimethylhydroxylamine hydrochloride (26.0 g, 26.7 mmol) in anhydrous CH2Cl2 (300 mL) at 0° C. was added dropwise 2-phenylbutyryl chloride (37.4 g, 20.5 mmol) dissolved in THF (100 mL). The reaction mixture was stirred overnight at RT. H2O (300 mL) was added, and the mixture was extracted with CH2Cl2 (2×200 mL). The combined extracts were washed successively with 5% aqueous HCl (300 mL), 5% aqueous NaHCO3 (300 mL), H2O (300 mL), and brine (300 mL). The mixture was dried over Na2SO4, filtered, and concentrated to afford 41.6 g (98%) of 14 as a colorless oil which was used without further purification. 1HNMR (400 MHz, CDCl3): δ 0.87 (t, J=7.3 Hz, 3H), 1.74 (h, J=7.1 Hz, 1H), 2.08 (h, J=7.1 Hz, 1H), 3.14 (s, 3H), 3.46 (s, 3H), 3.88 (br s, 1H), 7.19-7.33 (m, 5H).

Aufarbeitung

  1. extractionthe mixture was extracted with CH2Cl2 (2×200 mL)
  2. washThe combined extracts were washed successively with 5% aqueous HCl (300 mL), 5% aqueous NaHCO3 (300 mL), H2O (300 mL), and brine (300 mL)
  3. dry with materialThe mixture was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9e4dad0a664b471b8c53d2ab18558df0
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07442833B2

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