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

HRID 1414879노트

반응식

HRID 1414879 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f61ac5bbb5cd45468fc1fe0e51a24e1a
출처 데이터셋
uspto-grants-1977_01
특허 번호
US04002757

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