Pyridine → 6-Benzyloxy-3-dimethlamino-1,2,3,4-tetrahydrocarbazole

HRID 863475ノート

反応式

HRID 863475 の反応式
[CH3:1][N:2]([CH3:10])[CH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.Cl.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26]N)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1>C(O)C.O>[CH2:12]([O:19][C:20]1[CH:25]=[C:24]2[C:23](=[CH:22][CH:21]=1)[NH:26][C:6]1[CH2:7][CH2:8][CH:3]([N:2]([CH3:10])[CH3:1])[CH2:4][C:5]2=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochlorideHCID 103745454-(Dimethylamino)cyclohexan-1-one

生成物 1

HCID 128917786-Benzyloxy-3-dimethlamino-1,2,3,4-tetrahydrocarbazole収率 24.9%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

実験手順

To a solution of 3.78 gm (26.8 mMol) 4-dimethylamino-1-cyclohexanone and 6.69 gm (26.8 mMol) 4-benzyloxyphenylhydrazine hydrochloride in 50 mL ethanol were added 2.17 mL (26.8 mMol) pyridine. To this solution were added 5×10 mL portions of water and the reaction mixture then stored at 0° C. for 18 hours. The reaction mixture was then diluted with an additional 50 mL of water and the mixture extracted well with dichloromethane. The combined organic extracts were dried over sodium sulfate and the volatiles removed under reduced pressure. The residual oil was subjected to flash silica gel chromatography, eluting with 9:1 chloroform:methanol. Fractions shown to contain the desired product were combined and concentrated under reduced pressure to give 2.14 gm (24.9%) of the title compound.

後処理

  1. extractionthe mixture extracted well with dichloromethane
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. customthe volatiles removed under reduced pressure
  4. washeluting with 9:1 chloroform
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-eed351fb852b4036a5f91c2e5e4a373f
出典データセット
uspto-grants-1998_02
特許番号
US05721252

反応ノート

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