Sodium Iodide → 2-(4-Morpholinyl)ethyl 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl ether

HRID 1279717ノート

反応式

HRID 1279717 の反応式
Cl[CH2:2][CH2:3][O:4][C:5]1[C:17]2[C:16]3[C:11]4=[C:12]([O:18][CH2:19][CH:20]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[N:10]4[C:9]=2[CH:8]=[CH:7][CH:6]=1)[CH:13]=[CH:14][CH:15]=3.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:21]1([CH:20]2[N:10]3[C:11]4[C:16]([C:17]5[C:5]([O:4][CH2:3][CH2:2][N:27]6[CH2:32][CH2:31][O:30][CH2:29][CH2:28]6)=[CH:6][CH:7]=[CH:8][C:9]=53)=[CH:15][CH:14]=[CH:13][C:12]=4[O:18][CH2:19]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 121486367-(2-Chloroethoxy)-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazole

生成物 1

HCID 98446892-(4-Morpholinyl)ethyl 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl ether収率 61%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a mixture of 7-(2-chloroethoxy)-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazole (0.278 g, 0.764 mmol) in dry DMF (10 mL) is added morpholine (0.133 g, 1.53 mmol), sodium iodide (0.114 g, 0.764 mmol), and potassium carbonate (0.211 g, 1.53 mmol). The mixture is heated to 100° C. for 6 h. The mixture is removed from heat and stirred at room temperature for three days. The mixture is then partitioned between water and Et2O. The layers are separated and the organic layer is washed twice with water (50 mL) and then dried over anhydrous sodium sulfate and concentrated. Column chromatography (50 mL silica) using CH2Cl2/acetone/hexanes (7:2:1) gave 0.192 g (61%) of 2-(4-morpholinyl)ethyl 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl ether.

後処理

  1. customThe mixture is removed
  2. temperaturefrom heat
  3. customThe mixture is then partitioned between water and Et2O
  4. customThe layers are separated
  5. washthe organic layer is washed twice with water (50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-3fd228f1738f4f19a2d9a369b1906fa9
出典データセット
uspto-grants-2002_09
特許番号
US06448397B1

反応ノート

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