N-(4-benzyloxy-benzyl)-5-chloro-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide → 5-chloro-N-(4-hydroxy-benzyl)-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide

HRID 2244384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244384
C([O:8][C:9]1[CH:39]=[CH:38][C:12]([CH2:13][N:14]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[C:15](=[O:25])[C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[NH:23][CH3:24])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(OC(=O)C)C.[Pd]>[Cl:22][C:20]1[CH:19]=[CH:18][C:17]([NH:23][CH3:24])=[C:16]([CH:21]=1)[C:15]([N:14]([CH2:13][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:39][CH:38]=1)[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:35])[F:36])[CH:29]=1)=[O:25]

Komponenten

4

Edukt 1

HCID 68696190N-(4-benzyloxy-benzyl)-5-chloro-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide

Produkt 1

HCID 687030505-chloro-N-(4-hydroxy-benzyl)-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 930 mg (1.68 mmol) of N-(4-benzyloxy-benzyl)-5-chloro-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide (2 mmol) in 30 ml ethylacetate was hydrogenated over 300 mg of 5% Pd—C for 4 hours at RT. After completion of the reaction, the suspension was filtered, the catalyst washed with additional ethyl acetate and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel; heptane/-EtOAc 3:1) to give 339 mg 5-chloro-N-(4-hydroxy-benzyl)-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide (75%) as a white foam. MS (ISP) 463 (M+H)+.

Aufarbeitung

  1. customAfter completion of the reaction
  2. filtrationthe suspension was filtered
  3. washthe catalyst washed with additional ethyl acetate
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel; heptane/-EtOAc 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-c635393286bc46b2ae838c61d834da4d
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678818B2

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