Hydrochloric Acid → N1-[3-amino-4-(methyloxy)phenyl]-N1,N2,N2-trimethylglycinamide

HRID 1014391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1014391
[CH3:1][N:2]([CH3:24])[CH2:3][C:4]([N:6]([CH3:23])[C:7]1[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]([NH:13]C(=O)OC(C)(C)C)[CH:12]=1)=[O:5].Cl.C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[NH2:13][C:11]1[CH:12]=[C:7]([N:6]([CH3:23])[C:4](=[O:5])[CH2:3][N:2]([CH3:24])[CH3:1])[CH:8]=[CH:9][C:10]=1[O:21][CH3:22]

Komponenten

7

Edukt 4

HCID 313Hydrochloric Acid2×HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 594420081,1-dimethylethyl [5-[(N,N-dimethylglycyl)(methyl)amino]-2-(methyloxy)phenyl]carbamate

Produkt 1

HCID 59441934N1-[3-amino-4-(methyloxy)phenyl]-N1,N2,N2-trimethylglycinamideAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 1,1-dimethylethyl [5-[(N,N-dimethylglycyl)(methyl)amino]-2-(methyloxy)phenyl]carbamate (2.01 g, 5.96 mmol) in 1,4-dioxane (40 ml) was treated with 4.0M HCl in dioxanes (7.45 ml, 29.8 mmol) and stirred for 3 hours. Additional 4.0M HCl in dioxanes (7.45 ml, 29.8 mmol) was added and the reaction was stirred for 16 hours. The solution was poured into ethyl acetate, diluted with water, and neutralized by careful addition of solid potassium carbonate. The aqueous layer was washed with chloroform and the organic layers were combined, dried over sodium sulfate, filtered, and taken to a residue under reduced pressure to afford N1-[3-amino-4-(methyloxy)phenyl]-N1,N2,N2-trimethylglycinamide (1.19 g, 5.01 mmol, 84% yield) as a tan oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.78 (d, J=8.2 Hz, 1 H), 6.48 (d, J=2.4 Hz, 1 H), 6.41 (d, J=8.2 Hz, 1 H), 4.91 (br. s., 2 H), 3.77 (s, 3 H), 3.05 (s, 3 H), 2.82 (s, 2 H), 2.12 (s, 6 H).

Aufarbeitung

  1. stirringthe reaction was stirred for 16 hours
  2. washThe aqueous layer was washed with chloroform
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-c5610577d9014f6f94c291d1a2475b68
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981903B2

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