Water → {2-[4-(2-Azepan-1-ylethoxy)phenyl]ethyl}[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]methylamine

HRID 1434146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1434146
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:20]2[CH2:29][CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[C:25]([O:30][CH3:31])[CH:26]=3)[CH2:21]2)=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:39][CH2:40][N:41]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1.O>CN(C)C=O>[N:41]1([CH2:40][CH2:39][O:19][C:16]2[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][NH:10][CH2:9][C:7]3[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=3[CH:20]3[CH2:29][CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[C:25]([O:30][CH3:31])[CH:26]=4)[CH2:21]3)=[CH:14][CH:15]=2)[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 166251-(2-Chloroethyl)azepaneHCID 666275064-{2-{[5-Methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]methylamino}ethyl}phenol

Produkt 1

HCID 66626634{2-[4-(2-Azepan-1-ylethoxy)phenyl]ethyl}[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]methylamineAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 4-{2-{[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]methylamino}ethyl}phenol (160 mg) in N,N-dimethylformamide (3 ml) were sequentially added potassium carbonate (100 mg) and 1-(2-chloroethyl)azepane (110 mg), and the solution was stirred for 2 hours at 60° C. Water was added thereto followed by stirring, the solution was extracted with ethyl acetate, then sequentially washed with water and brine, and the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (157 mg).

Aufarbeitung

  1. stirringby stirring
  2. extractionthe solution was extracted with ethyl acetate
  3. washsequentially washed with water and brine
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-ace6744ebb9642d9b1b85f25d5f2b55c
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612114B2

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