Nitrogen → (2,6-Dimethoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)phenyl]-methanone

HRID 916859

Reaktionsgleichung

N#N.[CH3:3][O:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[CH:6]=1.[N:17]1([CH2:23][CH2:24][O:25][C:26]2[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl.O>[CH3:16][O:15][C:10]1[CH:9]=[CH:8][C:7]2[C:12](=[CH:13][CH:14]=[C:5]([O:4][CH3:3])[CH:6]=2)[C:11]=1[C:30]([C:29]1[CH:28]=[CH:27][C:26]([O:25][CH2:24][CH2:23][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:34][CH:33]=1)=[O:31]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

In a dry round bottom flask equipped with stir bar, temperature probe and N2 line, dissolve 2,6-dimethoxynaphthalene (1.0 eq) in CH2Cl2 (5 volume equivalents) at ambient temperature. Cool the solution to 0° C. in with an ice bath, and add 4-(2-piperidin-1-yl-ethoxy)-benzoyl chloride (1.1 eq). Add aluminum chloride (2.0 eq). Once the reaction is determined to be complete, quench the reaction slowly with 1 N NaOH and dilute with additional water and CH2Cl2. Wash the aqueous layer with (1×20 mL) of CH2Cl2. Combine the organic extracts and wash with brine and dry (Na2SO4). Recrystallize the crude product from methanol to give (2,6-dimethoxy-naphthalen-1-yl)[4(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (average yield 68%).

Aufarbeitung

customIn a dry round bottom flask equipped
customquench
customthe reaction slowly with 1 N NaOH
washWash the aqueous layer with (1×20 mL) of CH2Cl2
washwash with brine
dry with materialdry (Na2SO4)
customRecrystallize the crude product from methanol

Quellen und Nachweise

ORD-Eintrag: ord-3d8ec612189a4600be88781b87d7df3d
Quelldatensatz: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07271264B2

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