Dimethylformamide → 1-[4-(4-{[1-benzhydrylazetidin-3-yl]methoxy}phenyl)tetrahydro-2H-pyran-4-yl]-N,N-dimethylmethanamine

HRID 272995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272995
[CH3:1][N:2]([CH2:4][C:5]1([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)[CH3:3].Cl.[CH:19]([N:32]1[CH2:35][CH:34]([CH2:36]Cl)[CH2:33]1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH:19]([N:32]1[CH2:35][CH:34]([CH2:36][O:17][C:14]2[CH:15]=[CH:16][C:11]([C:5]3([CH2:4][N:2]([CH3:1])[CH3:3])[CH2:6][CH2:7][O:8][CH2:9][CH2:10]3)=[CH:12][CH:13]=2)[CH2:33]1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenolHCID 68576193HCID 68576193, Verbindung

Produkt 1

HCID 685784331-[4-(4-{[1-benzhydrylazetidin-3-yl]methoxy}phenyl)tetrahydro-2H-pyran-4-yl]-N,N-dimethylmethanamineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (1.15 g, 5.65 mmol), 1-benzhydryl-3-chloromethyl-azetidine hydrochloride (1.58 g, 5.13 mmol), N,N-dimethylformamide (32 ml) and potassium carbonate (2.84 g, 20.52 mmol) were reacted together according to general procedure B. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with 2M sodium hydroxide (3×50 ml), brine (3×50 ml), dried over magnesium sulphate, filtered and concentrated in vacuo to provide 1-[4-(4-{[1-benzhydrylazetidin-3-yl]methoxy}phenyl)tetrahydro-2H-pyran-4-yl]-N,N-dimethylmethanamine (1.82 g, 81%) as an off-white solid.

Aufarbeitung

  1. washThe organic layer was washed with 2M sodium hydroxide (3×50 ml), brine (3×50 ml)
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-972057df92844b5f9e0c23d8f9ae6a05
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456164B2

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