Triethylamine → HCID 69848839, Verbindung

HRID 352218

Reaktionsgleichung

Reaktionsgleichung von HRID 352218
[CH2:1]([O:3][C:4](=[O:13])[CH:5](Br)[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2].[CH3:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.CCN(CC)CC>ClCCl>[CH2:1]([O:3][C:4](=[O:13])[CH:5]([N:18]1[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]1)[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 21985933Ethyl 2-bromo-2-(pyridin-3-yl)acetate

Produkt 1

HCID 69848839HCID 69848839, VerbindungAusbeute 28,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Bromo-pyridin-3-yl-acetic acid ethyl ester (2.54 g; 10.2 mmol), was reacted in refluxing dichloromethane, overnight with 1-methylpiperazine (4.54 mL; 41.0 mmol; 4 equiv) and Et3N (5.8 mL; 41.0 mmol; 4 equiv). The reaction solution was evaporated to dryness, dissolved in CH2Cl2, washed five times with saturated NaHCO3 (aq), washed once with saturated NaCl (aq), dried with Na2SO4, filtered, and concentrated in vacuo. The resulting brown oil was purified with silica gel chromatography in a 3×17 cm glass column using a 2% methanol/chloroform (v/v) mobile phase. A second column eluted with 30% EtOAc/hexanes (v/v) followed by a step gradient of 0.5-3% methanol/CH2Cl2 (v/v) produced the desired product as a yellow oil (756 mg; 28% yield). MS(ES) calc'd: [M+H]+=263.1 m/z. Found: 263.1 m/z.

Aufarbeitung

  1. customThe reaction solution was evaporated to dryness
  2. dissolutiondissolved in CH2Cl2
  3. washwashed five times with saturated NaHCO3 (aq)
  4. washwashed once with saturated NaCl (aq)
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting brown oil was purified with silica gel chromatography in a 3×17 cm glass column
  9. washA second column eluted with 30% EtOAc/hexanes (v/v)

Quellen und Nachweise

ORD-Eintrag
ord-9551cb8e243a4eeca923e0326e56a426
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743794B2

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