methyl 4-[2-(N-benzyloxycarbonyl-N-methylamino)ethylamino]benzoate → Methyl 4-{[2-(methylamino)ethyl]amino}benzoate

HRID 354496Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 354496
C(O[C:9]([N:11]([CH2:13][CH2:14][NH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)C)=O)C1C=CC=CC=1>CO.[Pd]>[CH3:9][NH:11][CH2:13][CH2:14][NH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1

Komponenten

4

Edukt 1

HCID 23511696methyl 4-[2-(N-benzyloxycarbonyl-N-methylamino)ethylamino]benzoate

Produkt 1

HCID 23512192Methyl 4-{[2-(methylamino)ethyl]amino}benzoateAusbeute 78,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 4-[2-(N-benzyloxycarbonyl-N-methylamino)ethylamino]benzoate (1.26 g, 3.68 mmol) in MeOH (20 mL) was added 5 wt. Pd—C (700 mg), and the mixture was hydrogenated (3 atm) for 4 hr at room temp. The mixture was filtered, and the filtrate was evaporated under a reduced pressure to give 600 mg (78%) methyl 4-[2-(N-methylamino)ethylamino]benzoate as a colorless oil. 1H-NMR (CDCl3, 400 MHz) δ2.46 (s, 3H), 2.88 (t, 2H, J=5.5 Hz), 3.27 br s, 2H), 3.85 (s, 3H), 6.57 (d, 2H, J=8.8 Hz), 7.85 (d, 2H, J=8.8 Hz); MS (FAB) m/z 209 (M++1).

Aufarbeitung

  1. customfor 4 hr
  2. customat room temp
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4945fc860c104604afd81dd108e75a6e
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756378B2

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