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Piperidine → Ethyl 2-acetoxymethyl-4-(3-chlorophenyl)-6-methyl-5-(3-phenyl-2-propene-1-ylcarbamoyl)-1,4-dihydropyridine-3-carboxylate

HRID 1700341
ノート
印刷プレビュー

反応式

HRID 1700341 の反応式
O=[C:2]([CH3:16])[CH2:3][C:4]([NH:6][CH2:7][CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5].[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O.[NH:26]1CCCCC1.[C:32]([O:35][CH2:36][C:37](=O)[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])(=[O:34])[CH3:33].C([O-])(=O)C.[NH4+]>C1C=CC=CC=1.CC(O)C.O>[C:32]([O:35][CH2:36][C:37]1[NH:26][C:2]([CH3:16])=[C:3]([C:4](=[O:5])[NH:6][CH2:7][CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:21]([C:20]2[CH:23]=[CH:24][CH:25]=[C:18]([Cl:17])[CH:19]=2)[C:38]=1[C:39]([O:41][CH2:42][CH3:43])=[O:40])(=[O:34])[CH3:33]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 8082PiperidineHCID 114773-ChlorobenzaldehydeHCID 517165Ammonium AcetateHCID 11480907Ethyl 4-acetoxyacetoacetateHCID 53935748HCID 53935748、化合物

生成物 1

HCID 70158280Ethyl 2-acetoxymethyl-4-(3-chlorophenyl)-6-methyl-5-(3-phenyl-2-propene-1-ylcarbamoyl)-1,4-dihydropyridine-3-carboxylate

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 962Water溶媒HCID 3776Isopropanol溶媒2 回

反応条件

温度
120 °C

実験手順

652 mg (3.00 mmol) of 3-oxo-N-(3-phenyl-2-propene-1-yl)butyramide, 0.510 ml (3.00 mmol) of 3-chlorobenzaldehyde and 0.045 ml (0.30 mmol) of piperidine were heated under reflux in 37.5 ml of benzene overnight while water was removed. The reaction solution was washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue thus obtained, 564 mg (3.0 mmol) of ethyl 4-acetoxy-3-oxobutyrate and 278 mg (3.6 mmol) of ammonium acetate were heated at 80° C. under stirring in 15 ml of 2-propanol for four nights. The reaction mixture was then heated at 120° C. under stirring under atmospheric pressure for 4 hours while 2-propanol was evaporated. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/2) to obtain the title compound.

後処理

  1. customwas removed
  2. washThe reaction solution was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue thus obtained
  6. customwas evaporated
  7. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/2)

出典と根拠

ORDレコード
ord-41a7643709914e13bef254f4c94c4da6
出典データセット
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06350762B1

反応ノート

読み込み中…

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