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

HRID 616253

反応式

HRID 616253 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9174bcb22eaf457188bc6d948cb69ff0
出典データセット
uspto-grants-1978_02
特許番号
US04073796

関連ノート

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