Triethylamine → 5,6-dichloro-N-[3-(dimethylamino)propyl]-N-methylnicotinamide

HRID 1517319

Reaktionsgleichung

Reaktionsgleichung von HRID 1517319
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:7]([Cl:15])=[N:8][CH:9]=[C:10]([CH:14]=1)[C:11]([OH:13])=O.C(N(CC)CC)C.[CH3:23][N:24]([CH3:30])[CH2:25][CH2:26][CH2:27][NH:28][CH3:29]>O.O1CCCC1>[Cl:5][C:6]1[C:7]([Cl:15])=[N:8][CH:9]=[C:10]([CH:14]=1)[C:11]([N:28]([CH2:27][CH2:26][CH2:25][N:24]([CH3:30])[CH3:23])[CH3:29])=[O:13]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 2479875,6-Dichloronicotinic acid

Produkt 1

HCID 636953665,6-dichloro-N-[3-(dimethylamino)propyl]-N-methylnicotinamideAusbeute 0,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Thionyl chloride (15 ml) was added to 5,6-dichloronicotinic acid (2.0 g, 10.4 mmol), and stirred under a nitrogen atmosphere at 90° C. for 30 minutes. The reaction solution was concentrated under reduced pressure, and with cooling with ice, triethylamine (4.36 ml, 31.3 mmol) and N,N,N′-trimethylpropane-1,3-diamine (2.39 ml, 15.6 mmol) were added to a tetrahydrofuran solution (30 ml) of the obtained residue, and stirred at room temperature for 3 minutes. Saturated saline water was added to the reaction solution, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by amine-type silica gel column chromatography (Biotage NH, hexane:ethyl acetate=4:1 to 1:1) to obtain 5,6-dichloro-N-[3-(dimethylamino)propyl]-N-methylnicotinamide (3.21 mg) as an orange oil.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. stirringstirred at room temperature for 3 minutes
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by amine-type silica gel column chromatography (Biotage NH, hexane:ethyl acetate=4:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-1e66ed862a9f427783c27749ef41997f
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232284B2

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