4-Butyloxyaniline → N-(4-n-butoxyphenyl)-2-(1-benzyl-4-hydroxypiperidin-4-yl)acetamide

HRID 49961

反応式

HRID 49961 の反応式
[Li+].[CH2:2]([N:9]1[CH2:14][CH2:13][C:12]([CH2:16][C:17]([O-:19])=O)([OH:15])[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:20]([O:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)[CH2:21][CH2:22][CH3:23].P(Cl)(Cl)(Cl)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.N1C=CC=CC=1>[CH2:20]([O:24][C:25]1[CH:26]=[CH:27][C:28]([NH:29][C:17](=[O:19])[CH2:16][C:12]2([OH:15])[CH2:11][CH2:10][N:9]([CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:14][CH2:13]2)=[CH:30][CH:31]=1)[CH2:21][CH2:22][CH3:23]

参加物

7

反応物 4

HCID 203524-ButyloxyanilineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 69894340(1-Benzyl-4-hydroxypiperidin-4-yl) acetic acid lithium salt

生成物 1

HCID 17823865N-(4-n-butoxyphenyl)-2-(1-benzyl-4-hydroxypiperidin-4-yl)acetamide収率 24%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
7.5 °C

実験手順

To a solution of (1-benzyl-4-hydroxypiperidin-4-yl) acetic acid lithium salt (3.09 g) in methylene chloride (60 mL) were added 4-n-butoxyaniline (2.0 g) and pyridine (2.14 mL). Phosphorous oxychloride (1.19 mL) was added dropwise to the solution under cooling with an ice-sodium chloride, followed by stirring at 5 to 10° C. for 1 hour. The mixture was made alkaline with saturated aqueous sodium bicarbonate under cooling with an ice-water, and the solution was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography (elution solvent; methylene chloride:methanol=19:1 to 9:1) to obtain the titled compound (1.15 g).

後処理

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (elution solvent; methylene chloride:methanol=19:1 to 9:1)

出典と根拠

ORDレコード
ord-23334740640f45f081f14beef34c204b
出典データセット
uspto-grants-2004_03
特許番号
US06710060B2

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