Acetic Acid → 5-[4-(2-Hydroxyethyl)piperazin-1-ylmethyl]indole

HRID 20978

反応式

HRID 20978 の反応式
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)=O.C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C.[OH:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.CN(C1C=CN=CC=1)C.O>[OH:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][N:33]([CH2:1][C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[NH:8][CH:7]=[CH:6]3)[CH2:32][CH2:31]1

参加物

10

反応物 6

HCID 176Acetic AcidHCID 76771-(2-Hydroxyethyl)piperazineHCID 10340Sodium CarbonateHCID 90495Di-tert-butyl dicarbonateHCID 589040Indole-5-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 684922255-[4-(2-Hydroxyethyl)piperazin-1-ylmethyl]indole収率 132.2%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒2 回

実験手順

5-Formylindole (2.00 g, 13.8 mmol) was dissolved in acetonitrile (40 mL), and the solution was added with di-tert-butyldicarbonate (3.31 g, 15.2 mmol) and DMAP (16.8 mg, 0.138 mmol), followed by stirring at room temperature for 2.7 hours. The solution was added with a solution of N-(2-hydroxyethyl)piperazine (6.46 g, 49.6 mmol) in acetonitrile (15 mL), and acetic acid (14.2 mL, 248 mmol), then sodium triacetoxyborohydride (13.1 g, 62.0 mmol) was added thereto little by little, followed by stirring at room temperature for 2.5 hours. The reaction mixture was added with water and sodium carbonate to adjust the pH to 9, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (chloroform/methanol=9/1, 4/1) to obtain 5-[4-(2-hydroxyethyl)piperazin-1-ylmethyl]indole (4.73 g, yield 95%).

後処理

  1. stirringby stirring at room temperature for 2.5 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography (chloroform/methanol=9/1, 4/1)

出典と根拠

ORDレコード
ord-a23f19c4c3e742429592b0df512d02f8
出典データセット
uspto-grants-2010_06
特許番号
US07745641B2

関連ノート

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