Water → N-(1-benzyl-4-piperidinyl)-2,2,2-trifluoro-N-methylacetamide

HRID 1269774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269774
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:23]I.O>O1CCCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH3:23])[C:15](=[O:20])[C:16]([F:19])([F:17])[F:18])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1531300N-(1-benzylpiperidin-4-yl)-2,2,2-trifluoroacetamide

Produkt 1

HCID 20569912N-(1-benzyl-4-piperidinyl)-2,2,2-trifluoro-N-methylacetamideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-(1-benzyl-4-piperidinyl)-2,2,2-trifluoroacetamide (1.0 g, 3.49 mmol) was added to a suspension of 60%-sodium hydride (147 mg, 3.67 mmol) in tetrahydrofuran (20 ml) at room temperature and stirred for 30 minutes. Then, methyl iodide (0.239 ml, 3.84 mmol) was added thereto and stirred for 5 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=100/1) to obtain N-(1-benzyl-4-piperidinyl)-2,2,2-trifluoro-N-methylacetamide (731 mg, 70%).

Aufarbeitung

  1. stirringstirred for 5 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=100/1)

Quellen und Nachweise

ORD-Eintrag
ord-bf101155d04b46ec92ebfab75c7f6ea9
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199147B2

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