4-(Pyrrolidin-1-yl)butan-1-amine → 4-Chloro-N-[4-(1-pyrrolidinyl)butyl]-2-pyridinecarboxamide

HRID 491678

Reaktionsgleichung

Reaktionsgleichung von HRID 491678
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[N:11]1([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH2:15][CH2:14][CH2:13][CH2:12]1>C1COCC1.CCOC(C)=O>[N:11]1([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:8]([C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=2)=[O:9])[CH2:15][CH2:14][CH2:13][CH2:12]1

Komponenten

5

Edukt 2

HCID 27627624-(Pyrrolidin-1-yl)butan-1-amineHCID 110951464-chloropyridine-2-carbonyl Chloride

Produkt 1

HCID 859719314-Chloro-N-[4-(1-pyrrolidinyl)butyl]-2-pyridinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 4-chloro-pyridine-2-carbonyl chloride (8.88 g, 49 mmol) in THF (100 mL) was added at 0° C. 4-pyrrolidin-1-yl-butylamine (7.0 g, 49 mmol). The reaction was stirred for 18 h at RT. The mixture was diluted with EtOAc, washed several time with aqueous 6 N NaOH and then brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography using a gradient CH2Cl2/MeOH/NH4OH (100%, 0%, 0% to 90%, 10%, 1%). The pure fractions were combined and the solvents removed under vacuum. The title compound was obtained.

Aufarbeitung

  1. additionwas added at 0° C
  2. washwashed several time with aqueous 6 N NaOH
  3. dry with materialbrine, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography
  7. customthe solvents removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-62815154662f40f2b6291db7c0c97d64
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531553B2

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