2-Chloroquinoline-4-carbonyl chloride → 2-Chloro-N-(1-cyclohexylpyrrolidin-3-yl)quinoline-4-carboxamide

HRID 371616

Reaktionsgleichung

Reaktionsgleichung von HRID 371616
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:3]1.[Cl:13][C:14]1[CH:23]=[C:22]([C:24](Cl)=[O:25])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1>C(Cl)(Cl)Cl>[CH:7]1([N:4]2[CH2:5][CH2:6][CH:2]([NH:1][C:24]([C:22]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=[C:14]([Cl:13])[CH:23]=3)=[O:25])[CH2:3]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Komponenten

4

Edukt 2

HCID 754382-Chloroquinoline-4-carbonyl chlorideHCID 36700741-Cyclohexylpyrrolidin-3-amine

Produkt 1

HCID 203554052-Chloro-N-(1-cyclohexylpyrrolidin-3-yl)quinoline-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To 3.16 gm. (0.0195 mole) of 3-amino-1-cyclohexylpyrrolidine in 50 ml. of chloroform was added dropwise a solution of 3.5 gm. (0.015 mole) of 2-chloro-4-quinolinecarbonyl chloride in 50 ml. of chloroform. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate containing 10% isopropyl ether and dilute hydrochloric acid. The separated acid layer was made basic with dilute sodium hydroxide solution and extracted with chloroform. The chloroform solution was dried over sodium sulfate, concentrated and the residue recrystallized twice from isopropyl ether-ethyl acetate. The product (0.7 gm.; 13%) melted at 127°-219° C.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate containing 10% isopropyl ether and dilute hydrochloric acid
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform solution was dried over sodium sulfate
  5. concentrationconcentrated
  6. customthe residue recrystallized twice from isopropyl ether-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ab02c6ffd09e4230abcdae91bc596b11
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04087428

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