Methyl(2-(pyrrolidin-1-yl)ethyl)amine → 6-Chloro-N-methyl-N-(2-pyrrolidin-1-ylethyl)pyridine-3-sulfonamide

HRID 748518

Reaktionsgleichung

Reaktionsgleichung von HRID 748518
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][NH:13][CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:13]([CH3:12])[CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 295976Methyl(2-(pyrrolidin-1-yl)ethyl)amineHCID 27927922-Chloro-5-pyridinesulfonyl chloride

Produkt 1

HCID 632074446-Chloro-N-methyl-N-(2-pyrrolidin-1-ylethyl)pyridine-3-sulfonamideAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 6-chloropyridine-3-sulfonylchloride (636 mg, 3 mmol; described in: Naegeli, C. et al. Helv. Chim. Actal. 1938, 21, 1746-1750) in methylene chloride (10 mL) was added methyl-(2-pyrrolidin-1-ylethyl)amine (384 mg, 3 mmol; described in: J. Amer. Chem. Soc. 1955, 77, 3632-3634) dissolved in methylene chloride (10 mL) dropwise. The reaction mixture was stirred over night at room temperature followed by the extraction with aqueous HCl (3%). The acidic water layer was alkalized with an aqueous saturated solution of NaHCO3 and extracted with methylene chloride. The organic phase was dried (Na2SO4) and evaporated in vacuo to give 0.75 gram (80% yield) of the title compound: MS (ES) m/z 304 (M++1).

Aufarbeitung

  1. extractionfollowed by the extraction with aqueous HCl (3%)
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f74ad4236f434ba7ac93b1a8c2dd5aec
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399780B2

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