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

HRID 49961

반응식

HRID 49961 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

반응 조건

온도
7.5 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-23334740640f45f081f14beef34c204b
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710060B2

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