Water → 6-Methoxy-2-(methylethyl)-1-{4-[(2-piperidyl)ethoxy]benzyl}-1,2,3,4-tetrahydroisoquinoline

HRID 1357996Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1357996
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17](O)=[CH:16][CH:15]=1)[N:8]([CH:21]([CH3:23])[CH3:22])[CH2:7][CH2:6]2.Cl.ClCC[N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[C:34](=[O:37])([O-])[O-].[K+].[K+].O.[CH3:41]N(C)C=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:37][CH2:34][CH2:41][CH:33]3[CH2:32][CH2:31][CH2:30][CH2:29][NH:28]3)=[CH:18][CH:19]=1)[N:8]([CH:21]([CH3:22])[CH3:23])[CH2:7][CH2:6]2

Komponenten

6

Edukt 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 234407376-Methoxy-2-(methylethyl)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 536880276-Methoxy-2-(methylethyl)-1-{4-[(2-piperidyl)ethoxy]benzyl}-1,2,3,4-tetrahydroisoquinolineAusbeute 70 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 6-methoxy-2-(methylethyl)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline (0.212 g, 0.68 mmol), 2-chloroethylpiperidine hydrochloride (0.25 g, 1.36 mmol), and potassium carbonate (0.47 g, 3.4 mmol) in dimethylformamide (10 mL) was heated at 80° C. overnight. After cooling to room temperature, the mixture was poured into water and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was then purified by chromatography (SiO2, 0-15% methanol/CH2Cl2) to provide the title compound (0.201 g, 70% yield): ES-MS (m/z) 423 [M+H]+.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was then purified by chromatography (SiO2, 0-15% methanol/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-90aa056027d444d28ebf532b602203f5
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593322B1

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