Potassium Carbonate → 2-(4-Fluorophenyl)-1-(4-[2-(1-methyl(2-piperidyl))ethoxy]benzyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline

HRID 2119487

Reaktionsgleichung

Reaktionsgleichung von HRID 2119487
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:14]=3)[CH:9]2[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:41][CH2:42][CH:43]1[CH2:48][CH2:47][CH2:46][CH2:45][N:44]1[CH3:49].C(Cl)Cl.CO>CN(C=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:14]=3)[CH:9]2[CH2:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:41][CH2:42][CH:43]3[CH2:48][CH2:47][CH2:46][CH2:45][N:44]3[CH3:49])=[CH:31][CH:32]=2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 30165662-(2-Chloroethyl)-1-methylpiperidineHCID 21226129Dichloromethane methanolHCID 234407672-(4-Fluorophenyl)-1-(4-hydroxybenzyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 693163412-(4-Fluorophenyl)-1-(4-[2-(1-methyl(2-piperidyl))ethoxy]benzyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinolineAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-fluorophenyl)-1-(4-hydroxybenzyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline (0.500 g, 1.14 mmol) in DMF (5 ml) was added potassium carbonate (0.236 g, 1.7 nmmol) and the resulting mixture allowed to stir for twenty minutes. To the reaction mixture was added 2-(2-chloroethyl)-N-methyl piperidine (0.271 g, 1.37 mmol). The reaction was allowed to stir overnight. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated. The product was purified by radial chromatography (100% CH2Cl2, then CH2Cl2/MeOH, 95:5) to yield the title compound (0.043 g, 7% yield): ES−MS (m/z) 565 [M+H]+.

Aufarbeitung

  1. stirringto stir overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by radial chromatography (100% CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-ebbe60d92a97464bae3327034f63f199
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06686351B2

Verknüpfte Notizen

Wird geladen…