Potassium Carbonate → Methyl 2-(2-(benzyloxy)-5-(2-(4-propylpiperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate

HRID 454698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454698
C(=O)([O-])[O-].[K+].[K+].Cl.Cl.[CH2:9]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[CH2:10][CH3:11].[CH2:18]([O:25][C:26]1[CH:50]=[CH:49][C:48]([O:51][CH2:52][CH2:53]Br)=[CH:47][C:27]=1[C:28]([NH:30][C:31]1[CH:40]=[C:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:38]=[CH:37][C:32]=1[C:33]([O:35][CH3:36])=[O:34])=[O:29])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([O:25][C:26]1[CH:50]=[CH:49][C:48]([O:51][CH2:52][CH2:53][N:15]2[CH2:16][CH2:17][N:12]([CH2:9][CH2:10][CH3:11])[CH2:13][CH2:14]2)=[CH:47][C:27]=1[C:28]([NH:30][C:31]1[CH:40]=[C:39]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:38]=[CH:37][C:32]=1[C:33]([O:35][CH3:36])=[O:34])=[O:29])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 534225931-Propylpiperazine--hydrogen chloride (1/2)HCID 66990627Methyl 2-(2-(benzyloxy)-5-(2-bromoethoxy)benzamido)-4-phenylbenzoate

Produkt 1

HCID 66990571Methyl 2-(2-(benzyloxy)-5-(2-(4-propylpiperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoateAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Potassium carbonate (0.14 g) and 1-propylpiperazine dihydrochloride (0.12 g) were added to an acetone (1.6 mL) solution of methyl 2-(2-(benzyloxy)-5-(2-bromoethoxy)benzamido)-4-phenylbenzoate (0.080 g), followed by heating to reflux for 4 hours. After cooling the reaction mixture to room temperature, the solvent was evaporated under reduced pressure, and a saturated aqueous solution of sodium bicarbonate and chloroform were added to the residue. The organic layer was separated and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-90% chloroform/methanol] to obtain 0.081 g of methyl 2-(2-(benzyloxy)-5-(2-(4-propylpiperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate as a light yellow oily substance.

Aufarbeitung

  1. temperatureby heating
  2. temperatureto reflux for 4 hours
  3. customthe solvent was evaporated under reduced pressure
  4. additiona saturated aqueous solution of sodium bicarbonate and chloroform were added to the residue
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-90% chloroform/methanol]

Quellen und Nachweise

ORD-Eintrag
ord-efe2b8f4587c4480a9c3069251743a05
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492582B2

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