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Dimethylformamide → N-[3-(7-methoxyindol-3-yl)-2-propyl]-3-chloromandelamide

HRID 399018
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 399018
CN(C=O)C.[NH2:6][CH:7]([CH3:20])[CH2:8][C:9]1[C:17]2[C:12](=[C:13]([O:18][CH3:19])[CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=1)[CH:25]([OH:29])[C:26](O)=[O:27].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(OCC)(=O)C.C(N(CC)CC)C>[CH3:19][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[NH:11][CH:10]=[C:9]2[CH2:8][CH:7]([NH:6][C:26](=[O:27])[CH:25]([C:24]1[CH:30]=[CH:31][CH:32]=[C:22]([Cl:21])[CH:23]=1)[OH:29])[CH3:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 859813-Chloromandelic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 114242613-(2-Aminopropyl)-7-methoxyindole

Produkt 1

HCID 18969567N-[3-(7-methoxyindol-3-yl)-2-propyl]-3-chloromandelamideAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a DMF solution (80 ml) containing 3-(2-aminopropyl)-7-methoxyindole (12.24 g) and 3-chloromandelic acid (7.46 g) is added benzotriazole-N-oxytris(dimethylamino)phosphonium hexafluorophosphate (17.68 g), and then thereto is added dropwise triethylamine (9.8 ml). The mixture is stirred at room temperature for five hours, and to the reaction mixture is added ethyl acetate. The mixture is washed successively with water, 10% aqueous citric acid solution, water, a saturated aqueous sodium hydrogen carbonate solution, water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The mixture is evaporated to remove the solvent under reduced pressure, and the residue is purified by silica gel column chromatography (eluent; ethyl acetate/n-hexane=1:1→2:1) to give N-[3-(7-methoxyindol-3-yl)-2-propyl]-3-chloromandelamide (14.02 g) as an oily product.

Aufarbeitung

  1. washThe mixture is washed successively with water, 10% aqueous citric acid solution, water
  2. dry with materiala saturated aqueous sodium hydrogen carbonate solution, water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  3. customThe mixture is evaporated
  4. customto remove the solvent under reduced pressure
  5. customthe residue is purified by silica gel column chromatography (eluent; ethyl acetate/n-hexane=1:1→2:1)

Quellen und Nachweise

ORD-Eintrag
ord-dd99aebcf126462dba15c564736a5726
Quelldatensatz
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05817689

Notizen zur Reaktion

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