Methyl iodide → [4-(Benzyloxy)-3-methylquinolin-2-yl]methyl 4-(3-phenylpropanoyl)piperazine-1-carboxylate

HRID 384458ノート

反応式

HRID 384458 の反応式
N1([C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:23])[CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:10][CH2:9]2)=[O:7])C=CN=C1.CI.C(N(CC)CC)C.[CH2:33]([O:40][C:41]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[N:44]=[C:43]([CH2:51][OH:52])[C:42]=1[CH3:53])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(#N)C>[C:17]1([CH2:16][CH2:15][C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:52][CH2:51][C:43]3[C:42]([CH3:53])=[C:41]([O:40][CH2:33][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:50]4[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=4)[N:44]=3)=[O:7])[CH2:9][CH2:10]2)=[O:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 8471Triethylamine2 回HCID 595270961-(1H-imidazol-1-ylcarbonyl)-4-(3-phenylpropanoyl)piperazineHCID 68508380[4-(Benzyloxy)-3-methylquinolin-2-yl]methanol

生成物 1

HCID 59526968[4-(Benzyloxy)-3-methylquinolin-2-yl]methyl 4-(3-phenylpropanoyl)piperazine-1-carboxylate収率 72%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

To a solution of 1-(1H-imidazol-1-ylcarbonyl)-4-(3-phenylpropanoyl)piperazine (1.03 g) in acetonitrile (20 mL) was added dropwise methyl iodide (1.40 mL) and triethylamine (2.20 mL) at room temperature, followed by stirring at 60° C. for 5 hours. The reaction mixture was allowed to cool to room temperature, and then [4-(benzyloxy)-3-methylquinolin-2-yl]methanol (300 mg) was added thereto, followed by dropwise addition of triethylamine (0.50 mL) and stirring at 70° C. for 15 hours. The reaction mixture was concentrated under reduced pressure, and water (20 mL) was added to the residue, followed by extraction with ethyl acetate (50 mL). The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=90/10) to obtain [4-(benzyloxy)-3-methylquinolin-2-yl]methyl 4-(3-phenylpropanoyl)piperazine-1-carboxylate (405 mg).

後処理

  1. temperatureto cool to room temperature
  2. stirringstirring at 70° C. for 15 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and water (20 mL)
  4. additionwas added to the residue
  5. extractionfollowed by extraction with ethyl acetate (50 mL)
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=90/10)

出典と根拠

ORDレコード
ord-2d3d1705defa490abd83aa595e68e135
出典データセット
uspto-grants-2013_02
特許番号
US08367702B2

反応ノート

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