2-Pyridinemethanamine → Methyl 4-(2-(2-picolylamino)ethyl)benzoate

HRID 11841

Reaktionsgleichung

Reaktionsgleichung von HRID 11841
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH2:8].C(N(C(C)C)CC)(C)C.Br[CH2:19][CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][CH2:19][CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 195092-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 10586287Methyl 4-(2-bromoethyl)benzoate

Produkt 1

HCID 21973687Methyl 4-(2-(2-picolylamino)ethyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Commercially available 2-picolylamine (0.625 ml) was dissolved in toluene (15 ml) and diisopropylethylamine (0.715 ml) was added. After the addition of the compound obtained in Example 9-1 (499.7 mg), the mixture was stirred for two days at 80° C. After the reaction, toluene was added. The solution was washed with distilled water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed by istillation under reduced pressure, and the residue was purified by silica gel column chromatography (25 g, chloroform/methanol=25/1) to obtain the title compound (400.1 mg) as light brown oil.

Aufarbeitung

  1. additionwas added
  2. washThe solution was washed with distilled water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed by istillation under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (25 g, chloroform/methanol=25/1)

Quellen und Nachweise

ORD-Eintrag
ord-a78758e5b0fc4b538301b9f611812224
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098215B2

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