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

HRID 81680

Reaktionsgleichung

Reaktionsgleichung von HRID 81680
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-61ca127fc5f349d4ac5d2a6b922adcf8
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846700B2

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