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

HRID 1414880

반응식

HRID 1414880 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

To 3.16 gm. (0.0195mole) 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.

후처리

  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

출처 및 근거

ORD 기록
ord-87f00d114d904ee19aa0f48fa78ae185
출처 데이터셋
uspto-grants-1977_01
특허 번호
US04002757

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