Piperidine → (4-Benzylamino-phenyl)-piperidin-1-yl-methanone

HRID 2380967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2380967
[CH2:1]([NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.Cl.C(N=C=NCCCN(C)C)C.O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C>C(#N)C.O>[CH2:1]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:15])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 5

HCID 8082PiperidineHCID 8471TriethylamineHCID 8535464-(Benzylamino)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178526939HCID 178526939, Verbindung

Produkt 1

HCID 67130556(4-Benzylamino-phenyl)-piperidin-1-yl-methanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred suspension of 4-(benzylamino)benzoic acid (200 mg, 0.88 mmol) in acetonitrile (2 ml) was added piperidine (0.174 ml, 1.8 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (184 mg, 0.97 mmol), hydroxybenzotriazole hydrate (10 mg, catalytic) followed by triethylamine (0.31 ml, 2.2 mmol) and the reaction was stirred at room temperature for 16 hours. The reaction mixture was diluted with water (2 ml) and extracted with dichloromethane (2×2 ml). The organic phases were combined, washed with brine, dried over magnesium sulfate and then concentrated in vacuo. The residue was purified by flash column chromatography (SiO2) eluting with ethyl acetate/dichloromethane (1:4) to afford the title compound as an off white solid (122 mg, 47% yield).

Aufarbeitung

  1. extractionextracted with dichloromethane (2×2 ml)
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (SiO2)
  6. washeluting with ethyl acetate/dichloromethane (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-478b7767e245437aa82144000540f4fc
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258138B2

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