Acetic Acid → N,N-dimethyl-7-(piperazin-1-yl)benzofuran-2-carboxamide

HRID 383826

Reaktionsgleichung

Reaktionsgleichung von HRID 383826
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:22]3[O:21][C:20]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])=[CH:19][C:18]=3[CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)(=O)C.C(N(CC)CC)C>CO.[Pd]>[CH3:26][N:25]([CH3:27])[C:23]([C:20]1[O:21][C:22]2[C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:15][CH:16]=[CH:17][C:18]=2[CH:19]=1)=[O:24]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 8471TriethylamineHCID 596367707-(4-benzylpiperazin-1-yl)-N,N-dimethylbenzofuran-2-carboxamide

Produkt 1

HCID 59636743N,N-dimethyl-7-(piperazin-1-yl)benzofuran-2-carboxamideAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

The reaction mixture of 7-(4-benzylpiperazin-1-yl)-N,N-dimethylbenzofuran-2-carboxamide (0.70 g, 1.93 mmol) and acetic acid (0.44 mL, 7.70 mmol) in methanol (30 mL) was debenzylated in a H-cube for 3 h at 50° C. using Catcart 30 Pd/C cartridge. Triethylamine (1.1 mL, 7.9 mmol) was added and the solvent was removed in vacuo. The crude material was purified by flash chromatography (SiO2; DCM/MeOH; gradient 0-10%) to give 0.47 g (1.70 mmol) of product in 88% yield.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customThe crude material was purified by flash chromatography (SiO2; DCM/MeOH; gradient 0-10%)

Quellen und Nachweise

ORD-Eintrag
ord-7ae5005a03a04099be3c9d717e4b794e
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367676B2

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