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

HRID 49961

Reaktionsgleichung

Reaktionsgleichung von HRID 49961
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
7.5 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-23334740640f45f081f14beef34c204b
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710060B2

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