Piperidine → 5-(3-Phenyl-propene-1-yl) 3-(2-cyanoethyl) 4-(3-chlorophenyl)-2-methyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 890160ノート

反応式

HRID 890160 の反応式
[C:1]([O:7][CH2:8][CH2:9][C:10]#[N:11])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=C[CH:20]=1)C=O.[NH:21]1CCC[CH2:23][CH2:22]1.[C:27]([O:31][CH2:32][CH:33]=[CH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:30])[C:28]#[CH:29].C([O-])(=O)C.[NH4+]>C1C=CC=CC=1.C(O)(=O)C.O>[Cl:12][C:13]1[CH:20]=[C:5]([CH:3]2[C:28]([C:27]([O:31][CH:32]=[CH:33][CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[O:30])=[CH:29][NH:21][C:22]([CH3:23])=[C:2]2[C:1]([O:7][CH2:8][CH2:9][C:10]#[N:11])=[O:6])[CH:18]=[CH:15][CH:14]=1

参加物

9

反応物 5

HCID 8082PiperidineHCID 114773-ChlorobenzaldehydeHCID 517165Ammonium AcetateHCID 123604062-Cyanoethyl 3-oxobutanoateHCID 53746771(3-Phenyl-2-propene-1-yl) propiolate

生成物 1

HCID 695901655-(3-Phenyl-propene-1-yl) 3-(2-cyanoethyl) 4-(3-chlorophenyl)-2-methyl-1,4-dihydropyridine-3,5-dicarboxylate

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 241Benzene溶媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

466 mg (3.0 mmol) of (2-cyanoethyl) acetoacetate, 0.34 ml (3.0 mmol) of 3-chlorobenzaldehyde and 0.0297 ml of piperidine were heated under reflux in 3.0 ml of benzene for 7 hours while water was removed. The reaction liquid was washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was heated to 70° C together with 559 mg (3.0 mmol) of (3-phenyl-2-propene-1-yl) propiolate and 232 mg (3.0 mmol) of ammonium acetate under stirring in 3 ml of acetic acid for 13 hours, then at 120° C. under stirring for 4 hours. Acetic acid was evaporated under reduced pressure, and the residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/1) to obtain the title compound.

後処理

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

出典と根拠

ORDレコード
ord-013b148a9ba64dbb8a3e1b2e94f5fe00
出典データセット
uspto-grants-2006_02
特許番号
US06995179B2

反応ノート

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