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Quipazine → Ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylate

HRID 1714771
ノート
印刷プレビュー

反応式

HRID 1714771 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:7].[N:20]1([C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[N:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[CH:35][C:26]=1[N:20]1[CH2:25][CH2:24][N:23]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:7])[CH2:22][CH2:21]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 5011QuipazineHCID 8471TriethylamineHCID 23155883Ethyl 2-(5-bromopentanoylamino)cyclohex-1-enecarboxylate

生成物 1

HCID 23155633Ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylate収率 86%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

In 350 ml of toluene, 66.5 g of ethyl 2-(5-bromopentanoylamino)cyclohex-1-enecarboxylate as synthesized in above Step 4-1-B, 46.9 g of 2-piperazin-1-ylquinoline and 22.3 g of triethylamine were dissolved and heated under reflux for an overnight. The solvent was distilled off under reduced pressure, and ethyl acetate was added to the residue, followed by washing with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, and from which the solvent was distilled off under reduced pressure. Purifying the residue on silica gel column chromatography (n-hexane:ethyl acetate:methanol=1:6:0.2) to provide 79.8 g (86%) of ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylate.

後処理

  1. dissolutionwere dissolved
  2. temperatureheated
  3. temperatureunder reflux for an overnight
  4. distillationThe solvent was distilled off under reduced pressure, and ethyl acetate
  5. additionwas added to the residue
  6. washby washing with saturated aqueous sodium hydrogencarbonate solution
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. distillationfrom which the solvent was distilled off under reduced pressure
  9. customPurifying the residue on silica gel column chromatography (n-hexane:ethyl acetate:methanol=1:6:0.2)

出典と根拠

ORDレコード
ord-390e2549fd5a471fbfe81cbd08d9a018
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07799775B2

反応ノート

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