tert-Butyl methyl ether → N-[3-(2-dimethylaminoethoxy)4-methoxyphenyl]aminoacetaldehyde dimethyl acetal

HRID 1419823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1419823
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[NH2:9].[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH:19]=O.C(OC)(C)(C)C>C(O)C.[Pd]>[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19][NH:9][C:8]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:15])[CH3:1])[CH:7]=1

Komponenten

6

Edukt 3

HCID 15413tert-Butyl methyl etherHCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 105603983-(2-(Dimethylamino)ethoxy)-4-methoxyaniline

Produkt 1

HCID 10590199N-[3-(2-dimethylaminoethoxy)4-methoxyphenyl]aminoacetaldehyde dimethyl acetalAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 3-(2-dimethylaminoethoxy)-4-methoxyaniline (D14, 5.7 g, 0.027 mole) in ethanol (120 ml) was treated with a solution of 2,2-dimethoxyacetaldehyde in methyl tert-butyl ether (9.5 g of approx. 40% solution, 0.036 mole) and kept at room temperature for 16 hours. The solution was then hydrogenated over 10% Pd-C (0.6 g) at atmospheric pressure and temperature for 7 hours. The catalyst was removed by filtration through kieselguhr and the filtrate concentrated in vacuo. The residue was dissolved in ethyl acetate (100 ml), washed twice with water (2×60 ml), then dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 5% methanol/chloroform to afford the title compound as a red oil (5.4 g, 67%).

Aufarbeitung

  1. customThe catalyst was removed by filtration through kieselguhr
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  4. washwashed twice with water (2×60 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with 5% methanol/chloroform

Quellen und Nachweise

ORD-Eintrag
ord-2b32c839495a47178d9b91ba54b847cc
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05889022

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