2-Chloroquinoline-4-carbonyl chloride → N-Methyl-N-(1-cyclohexyl-3-pyrrolidinyl)-2-chloro-4-quinolinecarboxamide Hydrochloride

HRID 441404

Reaktionsgleichung

Reaktionsgleichung von HRID 441404
[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([NH:12][CH3:13])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:14][C:15]1[CH:24]=[C:23]([C:25](Cl)=[O:26])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1>C1C=CC=CC=1>[ClH:14].[CH3:13][N:12]([CH:9]1[CH2:10][CH2:11][N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:8]1)[C:25]([C:23]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([Cl:14])[CH:24]=1)=[O:26]

Komponenten

4

Edukt 2

HCID 754382-Chloroquinoline-4-carbonyl chlorideHCID 128957171-Cyclohexyl-N-methylpyrrolidin-3-amine

Produkt 1

HCID 20355402N-Methyl-N-(1-cyclohexyl-3-pyrrolidinyl)-2-chloro-4-quinolinecarboxamide Hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

To 12.7 g. (0.07 mole) of 1-cyclohexyl-3-methylaminopyrrolidine in dry benzene was added dropwise with stirring 15 g. (0.07 mole) of 2-chloroquinoline-4-carbonyl chloride in dry benzene. After 0.5 hr. the solution was extracted with dilute hydrochloric acid and the acidic solution made basic with sodium hydroxide solution and extracted with benzene. The benzene extracts were dried over sodium sulfate and concentrated. The residue was chromatographed on an aluminum silicate column eluting with a mixture of acetone benzene progressing from pure benzene to 50% acetone-benzene. The fractions containing the desired product were concentrated and the residue crystallized as the hydrochloride salt from isopropyl ether. The salt was recrystallized from isobutyl methyl ketone. Yield 10 g. (36%); m.p. 230-233° C.

Aufarbeitung

  1. extractionthe solution was extracted with dilute hydrochloric acid
  2. extractionextracted with benzene
  3. dry with materialThe benzene extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on an aluminum silicate column
  6. washeluting with a mixture of acetone benzene progressing from pure benzene to 50% acetone-benzene
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated
  9. customthe residue crystallized as the hydrochloride salt from isopropyl ether
  10. customThe salt was recrystallized from isobutyl methyl ketone

Quellen und Nachweise

ORD-Eintrag
ord-aae7ed0406dc44a3a37cacf030d2b370
Quelldatensatz
uspto-grants-1977_08
Patentnummer
US04039678

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