Aniline → N-phenyl-5-(4-(4-methoxyphenyl)piperazin-1-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-amine

HRID 1272307ノート

反応式

HRID 1272307 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][N:31]([C:34]3[C:35]([CH3:48])=[C:36]([CH3:47])[C:37]4[O:41][C:40]([CH3:43])([CH3:42])[CH:39](O)[C:38]=4[C:45]=3[CH3:46])[CH2:30][CH2:29]2)=[CH:24][CH:23]=1.CCCCCC.C(OCC)(=O)C>CO>[C:2]1([NH:1][CH:39]2[C:38]3[C:45]([CH3:46])=[C:34]([N:31]4[CH2:30][CH2:29][N:28]([C:25]5[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[CH:27][CH:26]=5)[CH2:33][CH2:32]4)[C:35]([CH3:48])=[C:36]([CH3:47])[C:37]=3[O:41][C:40]2([CH3:43])[CH3:42])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 6115AnilineHCID 521998p-Toluenesulfonic acid monohydrateHCID 21226206Ethyl acetate hexaneHCID 674202085-(4-(4-Methoxyphenyl)piperazin-1-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-ol

生成物 1

HCID 10298980N-phenyl-5-(4-(4-methoxyphenyl)piperazin-1-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-amine収率 87.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

Aniline (120 mg, 1.29 mmol) and p-toluenesulfonic acid monohydrate (25.0 mg, 0.131 mmol) were added to a solution of 5-(4-(4-methoxyphenyl)piperazin-1-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-ol (260 mg, 0.656 mmol) obtained in Reference Example 18 in methanol (3 ml) and the mixture was stirred at 60° C. for 120 hours. The resulting mixture was concentrated under reduced pressure. The residue was made to basic with 1N aqueous potassium carbonate and extracted with ethyl acetate. The organic extract was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified with basic column chromatography (hexane then hexane/ethyl acetate=25/1) to obtain 270 mg (yield 87%) of the title compound via recrystallization (methanol). mp. 90–94° C.

後処理

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with basic column chromatography (hexane

出典と根拠

ORDレコード
ord-75924681f1624c278172766aa01fef5c
出典データセット
uspto-grants-2007_04
特許番号
US07208495B2

反応ノート

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