Allyl bromide → HCID 10319122, Verbindung

HRID 2103734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2103734
[CH2:1]([N:3]([CH2:26][CH3:27])[C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:34](Br)[CH:35]=[CH2:36]>C(#N)C.O>[CH2:26]([N:3]([CH2:1][CH3:2])[C:4](=[O:25])[C:5]1[CH:6]=[CH:7][C:8]([N:11]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:12]2[CH2:17][CH2:16][N:15]([CH2:36][CH:35]=[CH2:34])[CH2:14][CH2:13]2)=[CH:9][CH:10]=1)[CH3:27]

Komponenten

6

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 10406550HCID 10406550, Verbindung2×

Produkt 1

HCID 10319122HCID 10319122, VerbindungAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of N,N-diethyl-4-[benzyl(piperidin-4-yl)amino]benzamide (Compound 8) (0.25 g, 0.684 mmole) in 10 mL of acetonitrile was added potassium carbonate (0.10 g, 0.752 mmole) and allyl bromide (0.08 g, 0.684 mmol). The reaction mixture was stirred for six days under Argon and then was diluted with water (50 mL). This solution was extracted three times with dichloromethane (50 mL). The organic extracts were combined, washed with sodium carbonate solution, dried (Na2SO4), and concentrated to provide a yellow foam. This material was purified on a flash silica gel column (5% methanol-chloroform to 10% methanol-chloroform) to provide 0.11 g (40%) of N,N-diethyl-4-[benzyl(1-allylpiperidin-4-yl)amino]benzamide as a colorless oil. MS (ES), m/z 406 (MH+). 300 MHz 1H NMR (CDCl3) δ1.17 (t, J=7.0 Hz, 6H), 1.68-1.90 (m, 4H), 2.06 (br t, J=10.6 Hz, 2H), 2.91-3.08 (m, 4H), 3.31-3.52 (m, 4H), 3.75-3.92 (br m, 1H), 4.52 (s, 2H), 5.09-5.25 (m, 2H), 5.75-5.95 (m, 1H), 6.65 (d, J=8.7 Hz, 2H), 7.15-7.38 (m, 7H).

Aufarbeitung

  1. extractionThis solution was extracted three times with dichloromethane (50 mL)
  2. washwashed with sodium carbonate solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto provide a yellow foam
  6. customThis material was purified on a flash silica gel column (5% methanol-chloroform to 10% methanol-chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-02398d8c3d644488bbff11ecd28fc1b2
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576105B2

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