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Methanamine, N-methoxy-, hydrochloride (1:1) → N-methoxy-N-methyl-4-Boc-piperazin-1-ylacetamide

HRID 586346
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 586346
Cl.[CH3:2][O:3][NH:4][CH3:5].C[Al](C)C.[C:10]([N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]([O:26]CC)=O)[CH2:19][CH2:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]>C(Cl)Cl>[CH3:2][O:3][N:4]([CH3:5])[C:24](=[O:26])[CH2:23][N:20]1[CH2:19][CH2:18][N:17]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:22][CH2:21]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 16682925TrimethylaluminumHCID 22321826tert-Butyl 4-(2-ethoxy-2-oxoethyl)piperazine-1-carboxylate

Produkt 1

HCID 22321660N-methoxy-N-methyl-4-Boc-piperazin-1-ylacetamideAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

N-Methoxy-N-methylamine hydrochloride (4.3 g, 44.1 mmol) was dissolved in methylene chloride (25 mL). The solution was cooled to −78° C., and a solution of trimethylaluminum (44.1 mL, 44.1 mmol, 1 M in heptane) was slowly added. The mixture was stirred at 0° C. for 30 min and was allowed to warm to room temperature and stirred for 30 min. The mixture was then cooled to 0° C., and a solution of ethyl 4-Boc-piperazin-1-ylacetate (10 g, 36.8 mmol) was added dropwise. After 15 min, the cold bath was removed and stirring continued overnight. The mixture was diluted with ethyl acetate and water. The layers were separated, and the water layer extracted with ethyl acetate. The organic layers were combined, washed with brine, dried (Na2SO4), filtered, and concentrated to provide N-methoxy-N-methyl-4-Boc-piperazin-1-ylacetamide as a light yellow oil (6.02 g, 57%) that solidified upon standing. The product was used without further purification.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringstirred for 30 min
  3. temperatureThe mixture was then cooled to 0° C.
  4. waitAfter 15 min
  5. customthe cold bath was removed
  6. stirringstirring continued overnight
  7. additionThe mixture was diluted with ethyl acetate and water
  8. customThe layers were separated
  9. extractionthe water layer extracted with ethyl acetate
  10. washwashed with brine
  11. dry with materialdried (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-88c5618a67234c60859d0b7dff1a4cb4
Quelldatensatz
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06936611B2

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