Tert-Butylamine → HCID 69850097, Verbindung

HRID 352215

Reaktionsgleichung

Reaktionsgleichung von HRID 352215
[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].[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15].CCN(CC)CC>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:13])[CH:5]([NH:18][C:14]([CH3:17])([CH3:16])[CH3:15])[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 21985933Ethyl 2-bromo-2-(pyridin-3-yl)acetate

Produkt 1

HCID 69850097HCID 69850097, VerbindungAusbeute 41,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Bromo-pyridin-3-yl-acetic acid ethyl ester (2.4 g; 9.8 mmol) was reacted in refluxing CH2Cl2, overnight with tert-butylamine (6.2 mL; 55.8 mmol; 6 equiv) and Et3N (2.8 mL; 19.6 mmol; 2 equiv). The reaction solution was evaporated to dryness, dissolved in CH2Cl2, washed six 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 6×8 cm glass column using a 30% EtOAc/hexanes (v/v) mobile phase. A total of 955 mg desired product was isolated (41% yield). MS(ES) calc'd: [M+H]+=237.1 m/z. Found: 237.1 m/z.

Aufarbeitung

  1. customThe reaction solution was evaporated to dryness
  2. dissolutiondissolved in CH2Cl2
  3. washwashed six 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 6×8 cm glass column

Quellen und Nachweise

ORD-Eintrag
ord-3499288dff3147a4924a45c2b553ec54
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743794B2

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